Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones

ABSTRACT

Intermediate compounds of the structural formula ##STR1## wherein R 60  is hydrogen; halogen; C 1  -C 2  alkyl; C 1  -C 2  alkoxy; nitro; cyano; C 1  -C 2  haloalkyl; or R a  SO n  -- wherein n is 0 or 2 and R a  is C 1  -C 2  alkyl, trifluoromethyl or difluoromethyl; or trifluoromethoxy or difluoromethoxy; R 61  is hydrogen or C 1  -C 4  alkyl; R 62  is hydrogen or C 1  -C 4  alkyl; or R 61  and R 62  together are C 2  -C 5  alkylene; R 63  C 1  -C 4  alkyl; R 64  is C 1  -C 4  alkyl; or R 63  R 64  together are C 2  -C 5  alkylene; R 65  and R 66  independently are (1) hydrogen; (2) halogen; (3) C 1  -C 4  alkyl; (4) C 1  -C 4  alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C 1  -C 4  haloalkyl; (9) R b  SO n  --wherein n is the integer 0, 1 or 2; and R b  is (a) C 1  -C 4  alkyl; (b) C 1  -C 4  alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR c  R d  wherein R c  and R d  independently are hydrogen or C 1  -C 4  alkyl; (11) R e  C(O)--wherein R e  is C 1  --C 4  alkyl or C 1  -C 4  alkoxy; or (12) --SO 2  NR c  R d  wherein R c  and R d  are as defined; and (13) --N(R c )C(O)R d  wherein R c  and R d  are defined.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a divisional application of Ser. No. 880,370, filedJune 30, 1986, now U.S. Pat. No. 4,780,127, which is acontinuation-in-part application of Ser. No. 872,067, filed June 9,1986, which is abandoned.

Applicants specifically incorporate by reference the contents of theabove listed U.S. patent applications.

BACKGROUND OF THE INVENTION

Compounds having the structural formula ##STR2## wherein X can be alkyl,n can be 0, 1, or 2, and R₁ can be phenyl or substituted phenyl aredescribed in Japanese Patent Application No. 84632-1974 as beingintermediates for the preparation of herbicidal compounds of the formula##STR3## wherein R₁, X, and n are as defined above and R₂ is alkyl,alkenyl, or alkynyl. Specifically taught herbicidal compounds of thislatter group are those where n is 2, X is 5,5-dimethyl, R₂ allyl and R₁is phenyl, 4-chlorophenyl or 4-methoxyphenyl.

The precursor intermediates for these three specifically taughtcompounds have no or almost no herbicidal activity.

DESCRIPTION OF THE INVENTION

Embodiment A of this invention relates to certain novel 2-(2-substitutedbenzoyl)-cyclohexane-1,3-diones as herbicides. The compounds of thisembodiment have the following structural formula ##STR4## wherein

R and R¹ are hydrogen, C₁ -C₄ alkyl, preferably methyl or isopropyl,R^(a) OC(O)--, where R^(a) is C₁ -C₄ alkyl; most preferably R and R¹ arehydrogen;

R² is chlorine, bromine, iodine or C₁ -C₄ alkoxy, preferably methoxy;most preferably R₂ is chlorine, bromine or methoxy;

R³, R⁴ and R⁵ independently are hydrogen or an aliphatic group,preferably: (1) hydrogen; (2) halogen, preferably chlorine or bromine;(3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ alkoxy, preferablymethoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -CH₄haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n) -- whereinR^(b) is C₁ -C₄ alkyl, preferably methyl, C₁ -C₄ haloalkyl, phenyl,benzyl, --NR^(d) R^(e) wherein R^(d) and R^(e) independently arehydrogen or C₁ -C₄ alkyl; and n is the integer 0, 1 or 2, preferably 2;##STR5## wherein R^(c) is C₁ -C₄ alkyl and R^(j) is hydrogen or C₁ -C₄alkyl, preferably methyl; (11) R^(f) C(O) wherein R^(f) is hydrogen, C₁-C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy; (12) --NR^(g) R^(h) whereinR^(g) and R^(h) independently are hydrogen or C₁ -C₄ alkyl; or lesspreferably (13) R³ and R⁴ together can form a ring structure with twoadjacent carbon atoms of the phenyl ring.

R³ and R⁴ can also be (14) C₃ -C₅ alkenyloxy (thio) optionallysubstituted, preferably with halogen or (15) C₃ -C₅ alkynyloxy (thio),optionally substituted, preferably with halogen.

Most preferably, R³ is chlorine, hydrogen, dimethylamino or methoxy.Preferably, R⁴ is hydrogen, chlorine, nitro, SO₂ CH₃, SO₂ N(CH₃)₂ ortrifluoromethyl. Preferably, R⁵ is hydrogen.

Embodiment A' of this invention is an herbicidal composition comprisingan herbicidally active 2-benzoyl-1,3-cyclohexanedione and an inertcarrier therefor. Preferably, the 2-position of the benzoyl moiety issubstituted with chlorine, bromine, iodine or C₁ -C₄ alkoxy; morepreferably chlorine, bromine or methoxy; most preferably chlorine. The5-position of the 1,3-cyclohexanedione moiety can be substituted withone or two C₁ -C₄ alkyl groups, preferably methyl, although such asubstitution is not preferred.

The compounds of Embodiment A of this invention can have the followingfour structural formulae because of tautomerism: ##STR6## wherein R, R¹,R², R³, R⁴ and R⁵ are as defined above.

The circled proton on each of the four tautomers is reasonably labile.These protons are acidic and can be removed by any base to give a salthaving an anion of the following four resonance forms: ##STR7## whereinR, R¹, R², R³, R⁴ and R⁵ are as defined above.

Examples of cations of these bases are inorganic cations such as alkalimetals, e.g. lithium, sodium, and potassium, alkaline earth metals, e.g.barium, magnesium, calcium and strontium or organic cations such assubstituted ammonium, sulfonium or phosphonium wherein the substituentis an aliphatic or aromatic group.

In the above description of the compounds of this invention, alkyl andalkoxy include both straight and branched configurations; for example,methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, andtert-butyl.

Embodiment B of this invention relates to certain novel 2-(2-substitutedbenzoyl)-cyclohexane-1,3-diones as herbicides. The compounds of thisembodiment have the following structural formula ##STR8## wherein

R¹⁰ is C₁ -C₆ alkyl, preferably C₁ -C₄, more preferably methyl;

R¹¹ is hydrogen or C₁ -C₆ alkyl, preferably C₁ -C₄, more preferablymethyl or ##STR9## wherein R^(a) is C₁ -C₄ alkyl or R¹⁰ and R¹¹ togetherare alkylene having 3 to 6 carbon atoms, most preferably R¹¹ is hydrogenor methyl;

R¹² is chlorine, bromine, iodine, fluorine or C₁ -C₄ alkoxy, preferablymethoxy; most preferably R¹² is chlorine, bromine or methoxy;

R¹³ and R¹⁴ independently are (1) hydrogen or an aliphatic group,preferably hydrogen; (2) halogen, preferably, fluorine, chlorine orbromine; (3) C₁ -C₄ alkyl, preferably methyl; (4) C₁ -C₄ aliphaticalkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro;(8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b) SO_(n)-- wherein R^(b) is C₁ -C₄ alkyl, preferably methyl, C₁ -C₄ haloalkyl,phenyl, benzyl, --NR^(d) R^(e) wherein R^(d) and R^(e) independently arehydrogen or C₁ -C₄ alkyl; and n is the integer 0, 1 or 2, preferably 2;##STR10## wherein R^(c) is C₁ -C₄ alkyl and R^(j) is hydrogen or C₁ -C₄alkyl, preferably methyl; (11) R^(f) C(O) wherein R^(f) is hydrogen, C₁-C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy; (12) --NR^(g) R^(h) whereinR^(g) and R^(h) independently are hydrogen or C₁ -C₄ alkyl; (13) C₁ -C₄alkylthio or less preferably (14) R¹³ and R¹⁴ together can form a ringstructure with two adjacent carbon atoms of the phenyl ring to whichthey are attached or less preferably (15) R¹³ and R¹⁴ are the groupsphenoxy or substituted phenoxy wherein the substituent is halogen orhalomethyl or both;

R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are independently the same or different and areselected from the group consisting of hydrogen, C₁ -C₆ alkyl, preferablyC₁ -C₄ alkyl, more preferably methyl, most preferably hydrogen ormethyl, and their salts;

provided, however, that R¹⁵ and R¹⁶ together may form a substituted orunsubstituted alkylene ring of 2-5 carbon atoms, the preferredsubstituent being 1 or 2 methyl groups.

More preferably, R¹³ is chlorine, hydrogen, methyl, alkylthio ormethoxy. Preferably R¹⁴ is hydrogen, chlorine, nitro, trifluoromethyl,or R^(b) SO_(n) wherein R^(b) is C₁ -C₄ alkyl, preferably methyl and nis the integer 0, 1 or 2, preferably 2.

The compounds of Embodiment B of this invention can have the followingfour structural formulae because of tautomerism: ##STR11## wherein R¹⁰,R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile.These protons are acidic and can be removed by any base to give a salthaving an anion of the following four resonance forms: ##STR12## whereinR¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkalimetals e.g. lithium, sodium, and potassium, alkaline earth metals, e.g.barium, magnesium, calcium and strontium, or organic cations such assubstituted ammonium, sulfonium or phosphonium wherein the substituentis an aliphatic or aromatic group.

The term "aliphatic group" is used form Embodiments A and B herein in abroad sense to cover a large class of organic groups characterized bybeing derived from (1) an acylic (open-chain structure) of the paraffin,olefin and acetylene hydrocarbon series and their derivatives or (2)alicyclic compounds. The aliphatic group can have from 1 to 10 carbonatoms.

The term "aromatic group" is used for Embodiments A and B herein in abroad sense to distinguish from the aliphatic group and includes a groupderived from (1) compounds having 6 to 20 carbon atoms and characterizedby the presence of at least one benzene ring, including monocyclic,bicyclic and polycyclic hydrocarbons and their derivatives and (2)heterocyclic compounds having 5 to 19 carbon atoms which are similar instructure and are characterized by having an unsaturated ring structurecontaining at least one atom other than carbon such as nitrogen, sulfurand oxygen and derivatives of these heterocyclic compounds.

In the above description of the compounds of this invention alkyl andalkoxy include both straight and branched configurations; for example,methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, andtert-butyl.

Embodiment C of this invention relates to certain novel2-(2'-cyanobenzoyl)cyclohexane-1,3-diones as herbicides. The compoundsof of this embodiment have the following structural formula ##STR13##wherein

R²¹ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl, most preferably R²¹ is hydrogen or methyl;

R²² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferablymethyl or ##STR14## wherein

R^(a) is C₁ -C₄ alkyl, most preferably R²² is hydrogen or methyl; or

R²¹ and R²² together are alkylene having 3 to 6 carbon atoms;

R²³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl; most preferably R²³ is hydrogen or methyl;

R²⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl; most preferably R²⁴ is hydrogen or methyl;

R²⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl; most preferably R²⁵ is hydrogen or methyl;

R²⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl, most preferably R²⁶ is hydrogen;

R²⁷ and R²⁸ independently are (1) hydrogen; (2) halogen, preferablychlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4)C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7)nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b)SO_(n) -- wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferablychloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogenor C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁-C₄ alkoxy; or (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are asdefined, with the proviso that R²⁷ is not attached to the 6-position.

Preferably, R²⁷ is in the 3-position. Most preferably R²⁷ is hydrogenand R²⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl, orR^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl.

Salts of the above-described compounds (as defined hereinafter) are alsothe subject of the instant invention.

The compounds of this embodiment can have the following four structuralformulae because of tautomerism: ##STR15## wherein R²¹, R²², R²³, R²⁴,R²⁵, R²⁶, R²⁷ and R²⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile.These protons are acidic and can be removed by any base to give a salthaving an anion of the following four resonance forms: ##STR16## whereinR²¹, R²², R²³, R²⁴, R²⁵, R²⁶, R²⁷ and R²⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkalimetals e.g. lithium, sodium, and potassium organic cations such assubstituted ammonium, sulfonium or phosphonium wherein the substitutentis an aliphatic or aromatic group.

Embodiment D of this invention relates to2-(2-nitrobenzoyl)-1,3-cyclohexanediones and their use as herbicides.

The compounds have a nitro substitution in the 2-position of the phenylmoiety of their compounds. The nitro substitution imparts exceptionalherbicidal activity to the compounds of this invention.

Embodiment D' of this invention is an herbicidal composition comprisingan herbicidally active 2-(2-nitrobenzoyl)-1,3-cyclohexanedione and aninert carrier therefor. The 4-, 5- and 6-positions of the1,3-cyclohexanedione moiety can be substituted, preferably with thegroups hereinafter recited. More preferably, the 1,3-cyclohexanedionemoiety has no substitution or the 4- or 6-positions are substituted withone or two methyl groups. The 3-, 4- and 5-positions of the benzoylmoiety can be substituted, preferably with the groups hereinafterrecited.

The novel compounds of Embodiment D have the following structuralformula ##STR17## wherein

R³¹ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl, most preferably R³¹ is hydrogen or methyl;

R³² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferablymethyl or ##STR18## wherein

R^(a) is C₁ -C₄ alkyl, most preferably R³² is hydrogen or methyl; or

R³¹ and R³² together are alkylene having 3 to 6 carbon atoms;

R³³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl; most preferably R³³ is hydrogen or methyl;

R³⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl; most preferably R³⁴ is hydrogen or methyl;

R³⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl; most preferably R³⁵ is hydrogen or methyl;

R³⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl, most preferably R³⁶ is hydrogen;

R³⁷ and R³⁸ independently are (1) hydrogen; (2) halogen, preferablychlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4)C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7)nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b)SO_(n) -- wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferablychloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogenor C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁-C₄ alkoxy; or (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are asdefined, with the proviso that R³⁷ is not attached to the 6-position.

Preferably, R³⁷ is in the 3-position. Most preferably R³⁷ is hydrogen orC₁ -C₄ alkoxy and R³⁸ is hydrogen, chlorine, bromine, fluorine,trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferablymethyl.

The term "C₁ -C₄ alkyl" includes methyl, ethyl, n-propyl, isopropyl,n-butyl, sec-butyl, isobutyl and t-butyl. The term "halogen" includeschlorine, bromine, iodine and fluorine. The terms "C₁ -C₄ alkoxy"includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy,isobutoxy and t-butoxy. The term "haloalkyl" includes the eight alkylgroups with one or more hydrogens replaced by chlorine, bromine, iodineor fluorine.

Salts of the above-described compounds (as defined hereinafter) are alsothe subject of the instant invention.

The compounds of this invention can have the following four structuralformulae because of tautomerism: ##STR19## wherein R³¹, R³², R³³, R³⁴,R³⁵, R³⁶, R³⁷ and R³⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile.These protons are acidic and can be removed by any base to give a salthaving an anion of the following four resonance forms: ##STR20## whereinR³¹, R³², R³³, R³⁴, R³⁵, R³⁶, R³⁷ and R³⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkalimetals e.g. lithium, sodium, and potassium or organic cations such assubstituted ammonium, sulfonium or phosphonium wherein the substituentis an aliphatic or aromatic group.

Embodiment E of this invention relates to2-(2-benzoyl)-1,3-cyclohexanediones and their use as herbicides.

Embodiment E' of this invention is an herbicidal composition comprisingan herbicidally active 2-(2-C₁ -C₄ alkylthio, C₁ -C₄ alkylsulfinyl or C₁-C₄ alkylsulfonyl benzoyl)-1,3-cyclohexanedione and an inert carriertherefor. The 4-, 5- and 6-positions of the 1,3-cyclohexanedione moietycan be substituted, preferably with the groups hereinafter recited. Morepreferably, the 1,3-cyclohexanedione moiety has no substitution or the4- or 6-positions are substituted with one or two methyl groups. The 3-,4- and 5-positions of the benzoyl moiety can be substituted, preferablywith the groups hereinafter recited.

The novel compounds of Embodiment E have the structural formula##STR21## wherein n is the integer 0, 1 or 2, preferably 2;

R⁴⁰ is C₁ -C₄ alkyl, preferably methyl;

R⁴¹ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl, most preferably R⁴¹ is hydrogen or methyl;

R⁴² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferablymethyl or ##STR22## wherein

R^(a) is C₁ -C₄ alkyl, most preferably R⁴² is hydrogen or methyl; or

R⁴¹ and R⁴² together are alkylene having 3 to 6 carbon atoms;

R⁴³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl; most preferably R⁴³ is hydrogen or methyl;

R⁴⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl; most preferably R⁴⁴ is hydrogen or methyl;

R⁴⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl; most preferably R⁴⁵ is hydrogen or methyl;

R⁴⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl, most preferably 4⁴⁶ is hydrogen;

R⁴⁷ and R⁴⁸ independently are (1) hydrogen; (2) halogen, preferablychlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4)C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7)nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b)SO_(n) -- wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferablychloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogenor C₁ -C₄ alkyl; (11) R^(e) C(O)--wherein R^(e) is C₁ -C₄ alkyl or C₁-C₄ alkoxy; or (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are asdefined, with the proviso that R⁴⁷ is not attached to the 6-position.

Preferably, R⁴⁷ is in the 3-position. Most preferably R⁴⁷ is hydrogen or3-chlorine and R⁴⁸ is hydrogen, chlorine, bromine, fluorine,trifluoromethyl, or R^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferablymethyl.

The term "C₁ -C₄ " alkyl includes methyl, ethyl, n-propyl, isopropyl,n-butyl, sec-butyl, isobutyl and t-butyl. The term "halogen" includeschlorine, bromine, iodide and fluorine. The term "C₁ -C₄ alkoxy"includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy,isobutoxy and t-butoxy. The term "haloalkyl" includes the eight alkylgroups with one or more hydrogens replaced by chloro, bromo, iodo orfluoro.

Salts of the above-described compounds (as defined hereinafter) are alsothe subject of the instant invention.

The compounds of this invention can have the following four structuralformulae because of tautomerism: ##STR23## wherein n, R⁴⁰, R⁴¹, R⁴²,R⁴³, R⁴⁴, R⁴⁵, R⁴⁶, R⁴⁷ and R⁴⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile.These protons are acidic and can be removed by any base to give a salthaving an anion of the following four resonance forms: ##STR24## whereinn, R⁴⁰, R⁴¹, R⁴², R⁴³, R⁴⁴, R⁴⁵, R⁴⁶, and R⁴⁷ and R⁴⁸ are as definedabove.

Examples of cations of these bases are inorganic cations such as alkalimetals e.g. lithium, sodium, and potassium, organic cations such assubstituted ammonium, sulfonium or phosphonium wherein the substitutentis an aliphatic or aromatic group.

Embodiment F of this invention relates to2-(2-alkylbenzoyl)-1,3-cyclohexanediones and their use as herbicides.

Embodiment F' of this invention is an herbicidal composition comprisingan herbicidally active 2-benzoyl-1,3-cyclohexanedione and an inertcarrier therefor wherein the 2-position of the benzoyl moiety issubstituted with C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, optionallysubstituted with halogen, more preferably methyl or trifluoromethyl andthe 4-position preferably is substituted with an electron withdrawinggroup, such as halogen, cyano, trifluoromethyl or nitro. The 4-, 5- and6-positions of the 1,3-cyclohexanedione moiety can be substituted,preferably with the groups hereinafter recited. More preferably, the1,3-cyclohexanedione moiety has no substitution or the 4- or 6-positionsare substituted with one or more methyl groups. The 3-, 4- and5-positions of the benzoyl moiety can be substituted, preferably withthe groups hereinafter recited.

The novel compounds of Embodiment F have the following structuralformula ##STR25## wherein R⁵⁰ is C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl,optionally substituted with halogen, more preferably methyl andtrifluoromethyl;

R⁵¹ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferabymethyl, most preferably R⁵¹ is hydrogen or methyl;

R⁵² is hydrogen; C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferablymethyl or ##STR26## wherein

R^(a) is C₁ -C₄ alkyl, most preferably R⁵² is hydrogen or methyl; or

R⁵¹ and R⁵² together are alkylene having 3 to 6 carbon atoms;

R⁵³ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, more preferabymethyl; most preferably R⁵³ is hydrogen or methyl;

R⁵⁴ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl; most preferably R⁵⁴ is hydrogen or methyl;

R⁵⁵ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl; most preferably R⁵⁵ is hydrogen or methyl;

R⁵⁶ is hydrogen or C₁ -C₄ alkyl, preferably C₁ -C₂ alkyl, morepreferably methyl, most preferably R⁵⁶ is hydrogen;

R⁵⁷ and R⁵⁸ independently are (1) hydrogen; (2) halogen, preferablychlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4)C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7)nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b)SO_(n) -- wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano, preferablychloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogenor C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁-C₄ alkoxy; or (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are asdefined, with the proviso that R⁵⁷ is not attached to the 6-position.

The term "C₁ -C₄ alkyl" includes methyl, ethyl, n-propyl, isopropyl,n-butyl, sec-butyl, isobutyl and t-butyl. The term "halogen" includeschlorine, bromine, iodine and fluorine. The term "C₁ -C₄ alkoxy"includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy,isobutoxy and t-butoxy. The term "haloalkyl" includes the eight alkylgroups with one or more hydrogens replaced by chloro, bromo, iodo orfluoro.

Preferably, R⁵⁷ is in the 3-position. Most preferably R⁵⁷ is hydrogenand R⁵⁸ is hydrogen, chlorine, bromine, fluorine, trifluoromethyl, orR^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl.

Salts of the above-described compounds (as defined hereinafter) are alsothe subject of the instant invention.

The compounds of this invention can have the following four structuralformulae because of tautomerism: ##STR27## wherein R⁵⁰, R⁵¹, R⁵², R⁵³,R⁵⁴, R⁵⁵, R⁵⁶, R⁵⁷ and R⁵⁸ are as defined above.

The circled proton on each of the four tautomers is reasonably labile.These protons are acidic and can be removed by any base to give a salthaving an anion of the following four resonance forms: ##STR28## whereinR⁵⁰, R⁵¹, R⁵³, R⁵⁴, R⁵⁵, R⁵⁶, R⁵⁷ and R⁵⁸ are as defined above.

Examples of cations of these bases are inorganic cations such as alkalimetals e.g. lithium, sodium, and potassium organic cations such assubstituted ammonium, sulfonium or phosphonium wherein the substituentis an aliphatic or aromatic group.

Embodiment G of this invention relates to2-benzoyl-1,3,5-cylcohexanetriones and their use as herbicides.

Embodiment G' of this invention is an herbicidal composition comprisingan herbicidally active 2-benzoyl-substituted-1,3,5-cyclohexanetrione andan inert carrier therefor. The 4- and 6-positions of the1,3,5-cyclohexanetrione moiety are preferably substituted with groupshereinafter defined, most preferably with all methyl groups. The benzoylmoiety can be substituted, preferably with the groups hereinafterrecited.

The novel compounds of Embodiment G have the following structuralformula ##STR29## wherein R⁶⁰ is hydrogen; halogen; C₁ -C₂ alkyl,preferably methyl; C₁ -C₂ alkoxy, preferably methoxy; nitro; cyano; C₁-C₂ haloalkyl, preferably trifluoromethyl; R^(a) SO_(n) -- wherein n is0 or 2, preferably 2 and R^(a) is C₁ -C₂ alkyl, preferably methyl,trifluoromethyl or difluoromethyl; or trifluoromethoxy ordifluoromethoxy. Preferably, R⁶⁰ is chlorine, bromine, C₁ -C₂ alkyl, C₁-C₂ alkoxy, trifluoromethyl, cyano, nitro, C₁ -C₂ alkylthio or C₁ -C₂alkylsulfonyl; more preferably chlorine, nitro, methyl, trifluoromethylor methylsulfonyl; and

R⁶¹ is hydrogen or C₁ -C₄ alkyl, preferably methyl;

R⁶² is hydrogen or C₁ -C₄ alkyl, preferably methyl; or

R⁶¹ and R⁶² together are C₂ -C₅ alkylene;

R⁶³ is C₁ -C₄ alkyl, preferably methyl;

R⁶⁴ is C₁ -C₄ alkyl, preferably methyl; or

R⁶³ and R⁶⁴ together are C₂ -C₅ alkylene;

R⁶⁵ and R⁶⁶ independently are (1) hydrogen; (2) halogen, preferablychlorine, fluorine or bromine; (3) C₁ -C₄ alkyl, preferably methyl; (4)C₁ -C₄ alkoxy, preferably methoxy; (5) trifluoromethoxy; (6) cyano; (7)nitro; (8) C₁ -C₄ haloalkyl, more preferably trifluoromethyl; (9) R^(b)SO_(n) -- wherein n is the integer 0, 1 or 2, preferably 2; and

R^(b) is

(a) C₁ -C₄ alkyl, preferably methyl;

(b) C₁ -C₄ alkyl substituted with halogen or cyano; preferablychloromethyl, trifluoromethyl or cyanomethyl;

(c) phenyl; or

(d) benzyl;

(10) --NR^(c) R^(d) wherein R^(c) and R^(d) independently are hydrogenor C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄ alkyl or C₁-C₄ alkoxy; (12) --SO₂ NR^(c) R^(d) wherein R^(c) and R^(d) are asdefined; or (13) --N(R^(c))C(O)R^(d) wherein R^(c) and R^(d) are asdefined.

Preferably R⁶⁵ is in the 3-position. More preferably R⁶⁵ is hydrogen,chlorine, fluorine, trifluoromethyl, cyano, C₁ -C₄ alkoxy or C₁ -C₄thioalkyl. Most preferably, R⁶⁵ is hydrogen. Preferably R⁶⁶ is in the4-position. Most preferably R⁶⁶ is halogen, cyano, trifluoromethyl, orR^(b) SO₂ wherein R^(b) is C₁ -C₄ alkyl, preferably methyl or C₁ -C₄haloalkyl, preferably chloromethyl, difluoromethyl or trifluoromethyl.

The term "C₁ -C₄ alkyl" includes methyl, ethyl, n-propyl, isopropyl,n-butyl, sec-butyl, isobutyl and t-butyl. The term "halogen" includeschlorine, bromine, iodine and fluorine. The terms "C₁ -C₄ alkoxy"includes methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy,isobutoxy and t-butoxy. The term "C₁ -C₄ haloalkyl" includes the alkylgroups defined above under C₁ -C₄ alkyl in which one or more hydrogensis replaced by chlorine, bromine, iodide or fluorine.

Salts of the above-described compounds (as defined hereinafter) areincluded within the scope of the instant invention.

The compounds of this invention can have the following four structuralformulae because of tautomerism: ##STR30## wherein R⁶⁰, R⁶¹, R⁶², R⁶³,R⁶⁴, R⁶⁵ and R⁶⁶ are as defined above.

The circled proton on each of the four tautomers is reasonably labile.These protons are acidic and can be removed by reaction with a base toform a salt having an anion of the following four resonance forms:##STR31## wherein R⁶⁰, R⁶¹, R⁶², R⁶³, R⁶⁴, R⁶⁵ and R⁶⁶ are as definedabove.

Examples of cations of these bases are inorganic cations such asalkalimetals, e.g., lithium, sodium and potassium; the alkaline earthmetals, e.g. calcium and magnesium or ammonium or organic cations suchas substituted ammonium, sulfonium, sulfoxonium or phosphonium whereinthe substituents are aliphatic or aromatic groups.

Those skilled in the art will recognize in considering the salts of thisinvention that varying degrees os association between the anion andcation will exist depending upon the nature of the cation. In someinstances with a suitable cation, such as copper, the salt can exist ina chelated form.

The compounds of this invention and their salts are active herbicides ofa general type. That is, they are herbicidally effective against a widerange of plant species. The method of controlling undesirable vegetationof the present invention comprises applying an herbicidally effectiveamount of the above-described compounds to the area where control isdesired.

The compounds of Embodiments A and A' of the present invention can beprepared by the following general method. ##STR32##

Generally, mole amounts of the dione and substituted benzoyl cyanide areused, along with a slight mole excess of zinc chloride. The tworeactants and the zinc chloride are combined in a solvent such asmethylene chloride. A slight mole excess of triethylamine is slowlyadded to the reaction mixture with cooling. The mixture is stirred atroom temperature for 5 hours.

The reaction product is worked up by conventional techniques.

The above-described substituted benzoyl cyanide can be preparedaccording to the teaching of T. S. Oakwood and C. A. Weisgerber, OrganicSynthesis Collected, Vol. III, pp. 122 (1955).

The following example teaches the synthesis of a representative compoundof Embodiments A and A' of this invention.

EXAMPLE 1-A,A' 2(2,4-Dichlorobenzoyl)-cyclohexane-1,3-dione ##STR33##

1,3-Cyclohexanedione [11.2 grams (g), 0.1 mole], 20.0 g (0.1 mole)2,4-dichlorobenzoyl cyanide and 13.6 g (0.11 mole) anhydrous, powderedzinc chloride were combined in 100 milliliters (ml) methylene chloride.Triethylamine (10.1 g, 0.12 mole) was slowly added with cooling. Thereaction mixture was stirred at room temperature for 5 hours and thenpoured into 2N hydrochloric acid. The aqueous phase was discarded andthe organic phase was washed with 150 ml 5% Na₂ CO₃ four times. Theaqueous washings were combined and acidified with HCl, extracted withmethylene chloride, dried and concentrated to yield 25.3 g of crudeproduct. The crude product was dissolved in ether and stirred with 250ml of 5% copper (II) acetate. The resulting copper salt was filtered,washed with ether and stirred with 6N hydrochloric acid to destroy thesalt. The extract was washed with ether to yield 22.15 grams of thedesired product m.p. 138°-140° C. (77.7% yield). The structure wasconfirmed by instrumental analysis.

The compounds of Embodiment B of the present invention can be preparedby the following general method. ##STR34##

Generally, mole amounts of the dione and substituted benzoyl cyanide areused, along with a slight mole excess of zinc chloride. The tworeactants and the zinc chloride are combined in a solvent such asmethylene chloride. A slight mole excess of triethylamine is slowlyadded to the reaction mixture with cooling. The mixture is stirred atroom temperature for 5 hours.

The reaction product is worked up by conventional techniques.

The above-described substituted benzoyl cyanide can be preparedaccording to the teaching of T. S. Oakwood and C. A. Weisgerber, OrganicSynthesis Collected, Vol. III, pp. 122 (1955).

The following example teaches the synthesis of a representative compoundof Embodiment B of this invention.

EXAMPLE 1-B 4,4-Dimethyl-2-(2,4-dichlorobenzoyl)-cyclohexane-1,3-dione##STR35##

4,4-Dimethyl-1,3-cyclohexanedione [14.0 grams (g), 0.1 mole], 20.0 g(0.1 mole) 2,4-dichlorobenzoyl cyanide and 13.6 g (0.11 mole) anhydrous,powdered zinc chloride were combined in 100 milliliters (ml) methylenechloride. Triethylamine (10.1 g, 0.12 mole) was slowly added withcooling. The reaction mixture was stirred at room temperature for 5hours and then poured into 2N hydrochloric acid. The aqueous phase wasdiscarded and the organic phase was washed with 150 ml 5% Na₂ CO₃ fourtimes. The aqueous washings were combined and acidified with HCl,extracted with methylene chloride, dried and concentrated to yield 25.3g of crude product. The crude product was chromatographed (2% AcOH/CH₂Cl₂) in 5 g aliquots then reduced on rotavap under reduced pressure at50° C. for 30 minutes to remove AcOH. This yielded an oil (40% yield).The structure was confirmed by instrumental analysis.

The compounds of Embodiment C of the present invention can be preparedby the following general method. ##STR36##

Generally, in step (1) mole amounts of the dione and substituted benzoylchloride are used, along with a slight mole excess of triethylamine. Thetwo reactants are combined in a solvent such as methylene chloride. Thetriethylamine is slowly added to the reaction mixture with cooling. Themixture is stirred at room temperature for several hours.

The reaction product is worked up by conventional techniques. ##STR37##

Generally, in step (2) a mole of the enol ester intermediate is reactedwith 1 to 4 moles of the triethylamine, preferably 2 moles of thetriethylamine and up to 0.5 mole, preferably 0.1 mole of a cyanidesource (e.g., potassium cyanide or acetone cyanohydrin). The mixture isstirred in a reaction pot for about one hour at room temperature and thedesired product is recovered by conventional techniques.

The above described substituted benzoyl chlorides can be prepared fromthe corresponding substituted benzoic acids according to the teaching ofReagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp.767-769 (1967). ##STR38## wherein R²⁷ and R²⁸ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety ofgeneral methods according to the teaching of The Chemistry of CarboxylicAcids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y.(1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson,J. Wiley and Sons, (1970).

The following are two representative examples of the methods describedtherein. ##STR39## wherein R²⁷ and R²⁸ are as previously defined.

In reaction (a) the substituted acetophenone is heated to reflux forseveral hours in an aqueous hypochlorite solution. The mixture is cooledand the reaction product is isolated by conventional techniques.##STR40## wherein R²⁷ and R²⁸ are as previously defined.

In reaction (b) the substituted toluene is heated to reflux in anaqueous solution of potassium kpermanganate for several hours. Thesolution is then filtered and the reaction product is isolated byconventional techniques.

The following example teaches the synthesis of a representative compoundof Embodiment C of this invention.

EXAMPLE 1-C 2-(2'-Cyanobenzoyl)-4,4-dimethyl-1,3-cyclohexanedione##STR41##

2-Cyanobenzoyl chloride (3.9 g, 24 mmol) and4,4-dimethyl-1,3-cyclohexanedione (3.3 g, 24 mmol) were dissolved in 75ml methylene chloride. Triethylamine (5.0 ml, 36 mmol) was addeddropwise and the resulting solution stirred for one and one-half hoursat room temperature. The solution was washed with water, 2 normalhydrochloric acid (2N HCl), 5% potassium carbonate solution (5% K₂ CO₃)and saturated sodium chloride solution (brine), dried over anhydrousmagnesium sulfate (MgSO₄) and concentrated under vacuum. The residue wasdissolved in 20 ml acetonitrile. Triethylamine (4.4 ml, 32 mmol) andacetone cyanohydrin (5 drops) were added and the solution stirred fortwo hours. After dilution with ether, the solution was washed with 2NHCl and extracted with 5% K₂ CO₃. The aqueous extract was acidified withconcentrated hydrochloric acid and extracted with ether. The ether waswashed with water and brine, dried (MgSO₄) and concentrated undervacuum. The residue was purified by silica gel chromatography, yielding1.2 g of a viscous oil which was identified as the desired compound bynuclear magnetic resonance spectroscopy, infrared spectroscopy and massspectroscopy.

The compounds of Embodiments D and D' of the present invention can beprepared by the following two-step general method.

The process proceeds via the production of an enol ester intermediate asshown in reaction (1). The final product is obtained by rearrangement ofthe enol ester as shown in reaction (2). The two reactions may beconducted as separate steps by isolation and recovery of the enol esterusing conventional techniques prior to conducting step (2), or byaddition of a cyanide source to the reaction medium after the formationof the enol ester, or in one step by inclusion of the cyanide source atthe start of reaction (1). ##STR42## wherein FR³¹ through R³⁸ andmoderate base are as defined and X is halogen, preferably chlorine, C₁-C₄ alkyl--C(O)--O--, C₁ -C₄ alkoxy--C(O)--O-- or ##STR43## wherein R³⁷and R³⁸ in this portion of the molecule are identical with those in thereactant shown above and the moderate base is as defined, preferablytri-C₁ -C₆ alkylamine, alkali metal carbonate or alkali metal phosphate.

Generally, in step (1) mole amounts of the dione and substituted benzoylreactant are used, along with a mole amount or excess of the base. Thetwo reactants are combined in an organic solvent such as methylenechloride, toluene, ethyl acetate or dimethylformamide. The base orbenzoyl reactant preferably are added to the reaction mixture withcooling. The mixture is stirred at 0° C.-50° C. until the reaction issubstantially complete. ##STR44## wherein the moderate base and R³¹through R³⁸ are as defined above.

Generally, in step (2) a mole of the enol ester intermediate is reactedwith 1 to 4 moles of the base, preferably about 2 moles of moderate baseand from 0.01 mole to about 0.5 mole or higher, preferably around 0.1mole of the cyanide source (e.g., potassium cyanide or acetonecyanohydrin). The mixture is stirred in a reaction pot until therearrangement is substantially complete at a temperature below 50° C.,preferably about 20° C. to about 40° C., and the desired product isrecovered by conventional techniques.

The term "cyanide source" refers to a substance or substances whichunder the rearangement conditions consists of or generates hydrogencyanide and/or cyanide anion.

The process is conducted in the presence of a catalytic amount of asource of cyanide anion and/or hydrogen cyanide, together with a molarexcess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium andpotassium cyanide; cyanohydrins of methyl alkylketones having from 1-4carbon atoms in the alkyl groups, such as acetone or methyl isobutylketone cyanohydrins; kcyanohydrins of benzaldehyde or of C₂ -C₅aliphatic aldehydes such as acetaldehyde, propionaldehyde, etc.,cyanohydrins; zinc cyanide; tri(lower alkyl) silyl cyanides, notablytrimethyl silyl cyanide; and hydrogen cyanide itself. Hydrogen cyanideis considered most advantageous as it produces relatively rapid reactionand is inexpensive. Among cyanohydrins the preferred cyanide source isacetone cyanohydrin.

The cyanide source is used in an amount up to about 50 mole percentbased on the enol ester. It may be used in as little as about 1 molepercent to produce an acceptable rate of reaction at about 40° C. on asmall scale. Larger scale reactions give more reproducible results withslightly higher catalyst levels of about 2 mole percent. Generally about1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enolester, of a moderate base. By the term "moderate base" is meant asubstance which acts as a base yet whose strength or activity as a baselies between that of strong bases such as hydroxides (which could causehydrolysis of the enol ester) and that of weak bases such asbicarbonates (which would not function effectively). Moderate basessuitable for use in this embodiment include both organic bases such astertiary amines and inorganic bases such as alkali metal carbonates andphosphates. Suitable tertiary amines include trialkylamines such astriethylamine. Suitable inorganic bases include potassium carbonate andtrisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per moleof enol ester, preferably about 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularlypotassium cyanide, a phase transfer catalyst may be included in thereaction. Particularly suitable phase transfer catalysts are the Crownethers.

A number of different solvents may be usable in this process, dependingon the nature of the acid chloride or the acylated product. A preferredsolvent for this reaction is 1,2-dichloroethane. Other solvents whichmay be employed, depending on the reactants or products include toluene,acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, andmethyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanidesource, the rearrangement may be conducted at temperatures up to about50° C.

The above described substituted benzoyl chlorides can be prepared fromthe corresponding substituted benzoic acids according to the teaching ofReagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp.767-769 (1967). ##STR45## wherein R³⁷ and R³⁸ are as previously defined.

The substituted benzoic acids can be prepared by a wide variety ofgeneral methods according to the teaching of The Chemistry of CarboxylicAcids and Esters, S. Pati, editor, J. Wiley and Sons, New York, N.Y.(1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson,J. Wiley and Sons, (1970).

The following are three representative examples of the methods describedtherein. ##STR46## wherein R³⁷ and R³⁸ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux inaqueous sulfuric acid for several hours. The mixture is cooled and thereaction product is isolated by conventional techniques. ##STR47##wherein R³⁷ and R³⁸ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux forseveral hours in an aqueous hypochlorite solution. The mixture is cooledand the reaction product is isolated by conventional techniques.##STR48## wherein R³⁷ and R³⁸ are as previously defined.

In reaction (c) the substituted toluene is heated to reflux in anaqueous solution of potassium permanganate for several hours. Thesolution is then filtered and the reaction product is isolated byconventional techniques.

The following examples teach the synthesis of representative compoundsof Embodiment D and D' of this invention.

EXAMPLE 1-D,D' 2-(2'-Nitrobenzoyl)-1,3-cyclohexanedione ##STR49##

2-Nitrobenzoyl chloride (5.0 g, 27 mmol) and cyclohexanedione (3.0 g, 27mmol) were dissolved in methylene chloride. Triethylamine (4.9 ml, 35mol) was added dropwise and the resulting solution stirred for one hour.The solution was washed with 2 normal hydrochloric acid (2N HCl), water,5% potassium carbonate solution and saturated sodium chloride solution,dried over anhydrous magnesium sulfate (MgSO₄) and concentrated undervacuum. The residue was dissolved in 20 ml acetonitrile. Triethylamine(1 equivalent) and potassium cyanide (40 mol %) were added and thesolution stirred for one hour at room temperature. After dilution withether, the solution was washed with 2N HCl and extracted with 5%potassium carbonate solution. The aqueous extract was acidified andether was added. Filtration of the resulting mixture yielded 3.2 g ofthe desired compound (m.p. 132°-135° C.) which was identified by nuclearmagnetic resonance spectroscopy, infrared spectroscopy and massspectroscoy.

EXAMPLE 2-D,D' 2-(2'-Nitrobenzoyl)-5,5-dimethyl-1,3-cyclohexanedione##STR50##

Triethylamine (3.4 ml, 25 mmol) was added dropwise to a methylenechloride solution of 2-nitrobenzoyl chloride (3.5 g, 19 mmol) and5,5-dimethylcyclohexanedione (2.4 g, 19 mmol). After stirring for onehour at room temperature an additional 3 equivalents of triethylamineand 0.4 ml acetone cyanohydrin were added. The solution was stirred for2.5 hours, then washed with 2N HCl and extracted with 5% potassiumcarbonate solution. The basic extracts were acidified with 2N HCl andextracted with ether. The ether portion was washed with saturated sodiumchloride solution, dried over anhydrous magnesium sulfate andconcentrated under vacuum. The residue was recrystallized from ethylacetate yielding 2.0 g of the desired compound (m.p. 130°-133° C.) whichwas identified as such by nuclear magnetic resonance spectroscopy,infrared spectroscopy and mass spectroscoy.

The compounds of Embodiments E and E' of the present invention can beprepared by the following two or three step general method.

The process proceeds via the production of an enol ester intermediate asshown in reaction (1). The final product is obtained by rearrangement ofthe enol ester as shown in reaction (2). The two reactions may beconducted as separate steps by isolation and recovery of the enol esterusing conventional techniques prior to conducting step (2), or byaddition of a cyanide source to the reaction medium after the formationof the enol ester, or in one step by inclusion of the cyanide source atthe start of reaction (1). ##STR51## wherein moderate base, and R⁴⁰through R⁴⁸ are defined herein, and X is halogen, preferably chlorine,C₁ -C₄ alkyl--C(O)--O--, C₁ -C₄ alkoxy--C(O)--O-- or ##STR52## whereinR⁴⁰, R⁴⁷ and R⁴⁸ in this portion of the moledule are identical withthose in the reactant shown above, and the moderate base is as defined,preferably tri-C₁ -C₆ alkylamine, alkali metal carbonate or alkali metalphosphate.

Generally, in step (1) mole amounts of the dione and substituted benzoylreactant are used, along with a mole amount or excess of the base. Thetwo reactants are combined in an organic solvent such as methylenechloride, toluene, ethyl acetate or dimethylformamide. The base orbenzoyl reactant preferably are added to the reaction mixture witcooling. The mixture is stirred at 0° C.-50° C. until the reaction issubstantially complete. ##STR53##

Generally, in step (2) a mole of the enol ester intermediate is reactedwith 1 to 4 moles of the base, preferably about 2 moles of moderate baseand from 0.01 mole to about 0.5 mole or higher, preferably around 0.1mole of the cyanide source (e.g., potassium cyanide oracetonecyanohydrin). The mixture is stirred in a reaction pot until therearangement is substantially complete at a temperature below 50° C.,preferably about 20° C. to about 40° C., and the desired product isrecovered by conventional techniques.

The term "cyanide sorce" refers to a substance or substances which underthe rearrangement conditions consists of or generates hydrogen cyanideand/or cyanide anion.

The process is conducted in the presence of a catalytic amount of asource of cyanide anion and/or hydrogen cyanide, together with a molarexcess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium andpotassium cyanide; cyanohydrins of methyl alkyl ketones having from 1-4carbon atoms in the alkyl groups, such as acetone or methyl isobutylketone cyanohydrins; cyanohydrins of benzaldehyde or of C₂ -C₅ aliphaticaldehydes siuch as acetaldehyde, propionaldehyde, etc., cyanohydrins;zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silylcyanide; and hydrogen cyanide itself. Hydrogen cyanide is consideredmost advantageous as it produces relatively rapid reaction and isinexpensive. Among cyanohydrins the preferred cyanide source is actonecyanohydrin.

The cyanide source is used in an amount up to about 50 mole percentbased on the enol ester. It may be used in as little as about 1 molepercent to produce an acceptable rate of reaction at about 40° C. on asmall scale. Larger scale reactions give more reproducible results withslightly higher catalyst levels of about 2 mole percent. Generally about1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enolester, of a moderate base. By the term "moderate base" is meant asubstance which acts as a base yet whose strength or activity as a baselies between that of strong bases such as hyroxides (which could causehydrolysis of the enol ester) and that of weak bases such asbicarbonates (which would not function effectively). Moderate basessuitable for use in this embodiment include both organic bases such astertiary amines and inorganic bases such as alkali metal carbonates andphosphtes. Suitable tertiary amines include trialkylamines such astriethylamine. Suitable inorganic bases include potassium carbonate andtrisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per moleof enol ester, preferably about 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularlypotassium cyanide, a phase transfer catalyst may be included in thereaction. Particularly suitable phase transfer catalysts are the Crownethers.

A number of different solvents may be usable in this process, dependingon the nature of the acid chloride or the acylated product. A preferredsolvent for ths reaction is 1,2-dichloroethane. Other solvents which maybe employed, depending on the reactants or products include toluene,acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, andmethyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanidesource, the rearrangment may be conducted at temperatures up to about50° C. ##STR54## wherein n is 1 or 2.

Generally in step (3), a mole of the reaction product of step (2) isreacted with a slight mole or two mole excess of an oxidizing agent suchas m-chloroperbenzoic acid after being dissolved in a solvent such asmethylene chloride. After completion of the reaction, the resultingmixture is stripped under vacuum. The residue is purified by silica gelchromatography to yield the desired product.

The above described substituted benzoyl chlorides can be prepared fromthe corresponding substituted benzoic acids according to the teaching ofReagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp.767-769 (1967). ##STR55## wherein R⁴⁰, R⁴⁷ and R⁴⁸ are as previouslydefined.

The substituted benzoic acids can be prepared by a wide variety ofgeneral methods according to the teaching of The Chemistry of CarboxylicAcids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y.(1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson,J. Wiley and Sons, (1970).

The following are three representative examples of the methods describedtherein. ##STR56## wherein R⁴⁰, R⁴⁷ and R⁴⁸ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux inaqueous sulfuric acid for several hours. The mixture is cooled and thereaction product is isolated by conventional techniques. ##STR57##wherein R⁴⁰, R⁴⁷ and R⁴⁸ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux forseveral hours in an aqueous hypochlorite solution. The mixture is cooledand the reaction product is isolated by conventional techniques.##STR58## wherein R⁴⁰, R⁴⁷ and R⁴⁸ are as defined and X is chlorine,bromine or iodine.

In reaction (c) the substituted aromatic halide is allowed to react withmagnesium in a solvent such as ether. The solution is then poured overcrushed dry ice and the benzoic acid is isolated by conventionaltechniques.

The following examples teach the synthesis representative compounds ofEmbodiments E and E' of this invention.

EXAMPLE 1-E,E'2-(2'-Methylthiobenzoyl)-4,4,6-trimethyl-1,3-cyclohexanedione ##STR59##

2-Methylthiobenzoyl chloride (7.2 g, 39 mmol) and4,4,6-trimethylcyclohexanedione (5.0 g, 39 mmol) were dissolved inmethylene chloride. Triethylamine (7.0 ml, 50 mmol) was added dropwiseand the resulting solution stirred for one hour at room temperature. Thesolution was washed with 2 normal hydrochloric acid (2N HCl), 5%potassium carbonate solution (5% K₂ CO₃) and saturated sodium chloridesolution (brine), dried over anhydrous magnesium sulfate (MgSO₄) andconcentrated under vacuum. The residue was dissolved in 20 mlacetonitrile. Triethylamine (2.5 equivalents) and acetone cyanohydrin(0.4 ml) were added and the solution stirred for 45 minutes at roomtemperature. After dilution with ether, the solution was washed with 2NHCl and extracted with 5% K₂ CO₃. The aqueous extract was acidified withhydrochloric acid and extracted with ether. The ether was washed withbrine, dried (MgSO₄) and concentrated under vacuum. The residue waspurified by trituration with ether, yielding 5.0 g of a viscous oilwhich was identified as the desired compound by nuclear magneticresonance spectroscopy (nmr), infrared spectroscopy (ir) and massspectroscopy (ms).

EXAMPLE 2-E,E'2-(2'-Methanesulfonylbenzoyl)-4,4,6-trimethyl-1,3-cyclohexanedione##STR60##

The benzoyl cyclohexanedione prepared in Example 1 (2.5 g, 7.9 mmol) wasdissolved in 40 ml methylene chloride. m-Chloroperbenzoic acid (3.5 g,16 mmol) was added and the resulting solution was stirred for 45minutes. The solution was concentrated under vacuum. Purification of theresidue by silica gel chromatography yielded 1.7 g of a viscous oilwhich was identified as the desired compound by nmr, ir and ms.

EXAMPLE 3-E,E'2-(4'-Trifluoromethyl-2'-methanesulfinylbenzoyl)-4,4-dimethyl-1,3-cyclohexanedione##STR61##

2-(4'-Trimethylfluoromethyl-2'-methylthiobenzoyl)-4,4-dimethyl-1,3-cyclohexanedione(5.0 g, 14 mmol) (which was prepared according to the method ofExample 1) was dissolved in 50 ml methylene chloride. A solution ofm-chloroperbenzoic acid (2.4 g-80%, 14 mmol) in 50 ml methylene chloridewas added dropwise and the resulting solution was stirred for threehours at room temperature. After concentration under vacuum, the residuewas dissolved in ether and washed with 1% hydrochloric acid. A 5%copper(II) acetate solution was added to the ether fraction, followed byhexane. The liquid phase was decanted and the remaining gummy solidstirred with 6N HCl and ether. The ether layer was dried (MgSO₄) andconcentrated to give 4.7 of a thick yellow solid. Purification on acentrifugally accelerated thin layer chromatograph (4 mm silica gel,50:50:1 hexane:ethyl acetate:acetic acid-eluent) yielded 2.4 g of aviscous oil which was identified as the desired compound by nmr, ir andms.

The compounds of Embodiments F and F' of the present invention can beprepared by the following two-step general method.

The process proceeds via the production of an enol ester intermediate asshown in reaction (1). The final product is obtained by rearrangement ofthe enol ester as shown in reaction (2). The two reactions may beconducted as separate steps by isolation and recovery of the enol esterusing conventional techniques prior to conducting step (2), or byaddition of a cyanide source to the reaction medium after the formationof the enol ester, or in one step by inclusion of the cyanide source atthe start of reaction (1). ##STR62## wherein R⁵⁰ through R⁵⁸ are asdefined and X is halogen, preferably chlorine, C₁ -C₄ alkyl--C(O)--O--,C₁ -C₄ alkoxy--C(O)--O-- or ##STR63## wherein R⁵⁰, R⁵⁷ and R⁵⁸ in thisportion of the molecule are identical with those in the reactant shownabove and the moderate base is as defined, preferably tri-C₁ -C₆alkylamine, alkali metal carbonate or alkali metal phosphate.

Generally, in step (1) mole amounts of the dione and substituted benzoylreactant are used, along with a mole amount or excess of the base. Thetwo reactants are combined in an organic solvent such as methylenechloride, toluene, ethyl acetate or dimethylformamide. The base orbenzoyl reactant preferably are added to the reaction mixture withcooling. The mixture is stirred at 0° C.-50° C. until the reaction issubstantially complete.

The reaction product is worked up by conventional techniques. ##STR64##

Generally, in step (2) a mole of the enol ester intermediate is reactedwith 1 to 4 moles of the base, preferably about 2 moles of moderate baseand from 0.01 mole to about 0.5 mole or higher, preferably around 0.1mole of the cyanide source (e.g., potassium cyanide or acetonecyanohydrin). The mixture is stirred in a reaction pot until therearrangement is substantially complete at a temperature below 80° C.,preferably about 20° C. to about 40° C., and the desired product isrecovered by conventional techniques.

The term "cyanide source" refers to a substance or substances whichunder the rearrangement conditions consists of or generates hydrogencyanide and/or cyanide anion.

The process is conducted in the presence of a catalytic amount of asource of cyanide anion and/or hydrogen cyanide, together with a molarexcess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium andpotassium cyanide; cyanohydrins of methyl alkyl ketones having from 1-4carbon atoms in the alkyl groups, such as acetone or methyl isobutylketone cyanohydrins; cyanohydrins of benzaldehyde or of C₂ -C₅ aliphaticaldehydes such as acetaldehyde, propionaldehyde, etc., cyanohydrins;zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silylcyanide; and hydrogen cyanide itself. Hydrogen cyanide is consideredmost advantageous as it produces relatively rapid reaction and isinexpensive. Among cyanohydrins the preferred cyanide source is acetonecyanohydrin.

The cyanide source is used in an amount up to about 50 mole percentbased on the enol ester. It may be used in as little as about 1 molepercent to produce an acceptable rate of reaction at about 40° C. on asmall scale. Larger scale reactions give more reproducible results withslightly higher catalyst levels of about 2 mole percent. Generally about1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enolester, of a moderate base. By the term "moderate base" is meant asubstance which acts as a base yet whose strength or activity as a baselies between that of strong bases such as hydroxides (which could causehydrolysis of the enol ester) and that of weak bases such asbicarbonates (which would not function effectively). Moderate basessuitable for use in this embodiment include both organic bases such astertiary amines and inorganic bases such as alkali metal carbonates andphosphates. Suitable tertiary amines include trialkylamines such astriethylamine. Suitable inorganic bases include potassium carbonate andtrisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per moleof enol ester, preferably about 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularlypotassium cyanide, a phase transfer catalyst may be included in thereaction. Particularly suitable phase transfer catalysts are the Crownethers.

A number of different solvents may be usable in this process, dependingon the nature of the acid chloride or the acylated product. A preferredsolvent for this reaction is 1,2-dichloroethane. Other solvents whichmay be employed, depending on the reactants or products include toluene,acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, andmethyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanidesource, the rearrangement may be conducted at temperatures up to about50° C.

The above described substituted benzoyl chlorides can be prepared fromthe corresponding substituted benzoic acids according to the teaching ofReagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp.767-769 (1967). ##STR65## wherein R⁵⁰, R⁵⁷ and R⁵⁸ are as previouslydefined.

The substituted benzoic acids can be prepared by a wide variety ofgeneral methods according to the teaching of The Chemistry of CarboxylicAcids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y.(1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson,J. Wiley and Sons, (1970).

The following are four representative examples of the methods describedtherein. ##STR66## wherein R⁵⁰, R⁵⁷ and R⁵⁸ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux inaqueous sulfuric acid for several hours. The mixture is cooled and thereaction product is isolated by conventional techniques. ##STR67##wherein R⁵⁰, R⁵⁷ and R⁵⁸ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux forseveral hours in an aqueous hypochlorite solution. The mixture is cooledand the reaction product is isolated by conventional techniques.##STR68## wherein R⁵⁰, R⁵⁷ and R⁵⁸ are as defined and X is chlorine,bromine or iodine.

The substituted aromatic halide is allowed to react with magnesium in asolvent such as ether. The solution is then poured over crushed dry iceand the benzoic acid is isolated by conventional techniques.

The following example teachs the synthesis of a representative compoundof Embodiments F and F' of this invention.

EXAMPLE 1-F,F'2-(4'-Bromo-2'-trifluoromethylbenzoyl)-4,4,6-trimethyl-1,3-cyclohexanedione##STR69##

4-Bromo-2-trifluoromethylbenzoyl chloride (4.3 g, 15 mmol) and4,4,6-trimethyl-1,3-cyclohexanedione (2.3 g, 15 mmol) were dissolved in100 ml methylene chloride. The solution was cooled with an ice bath andtriethylamine (2.1 ml, 15 mmol) in 10 ml methylene chloride was addeddropwise. The ice bath was then removed and the resulting solutionstirred for 30 minutes at room temperature. The solution was washed with2N hydrochloric acid (2N HCl), 5% potassium carbonate solution (5% K₂CO₃) and saturated sodium chloride solution (brine), dried overanhydrous magnesium sulfate (MgSO₄) and concentrated under vacuum. Theresidue (5.1 g) was dissolved in 20 ml acetonitrile. Triethylamine (3.5ml, 25 mmol) and 0.4 ml acetone cyanohydrin were added and the solutionstirred for two hours at room temperature while protected by a dryingtube (calcium sulfate). After dilution with ether, the solution waswashed with 2N HCl and extracted with 5 % K₂ CO₃. The aqueous extractwas acidified with concentrated hydrochloric acid and extracted withether. The ether was washed with brine, dried (MgSO₄) and concentratedunder vacuum. The resulting oil was purified on a silica gel column(80:20:1 hexane:ethyl acetate:acetic acid-eluent), yielding 1.5 g of aviscous oil which was identified as the desired compound by nuclearmagnetic resonance spectroscopy, infrared spectroscopy and massspectroscopy.

The compounds of Embodiment G and G' of the present invention can beprepared by the following two-step general method.

The process proceeds via the production of an enol ester intermediate asshown in reaction (1). The final product is obtained by rearrangement ofthe enol ester as shown in reaction (2). The two reactions may beconducted as separate steps by isolation and recovery of the enol esterusing conventional techniques prior to conducting step (2), or byaddition of a cyanide source to the reaction medium after the formationof the enol ester, or in one step by inclusion of the cyanide source atthe start of reaction (1). ##STR70## wherein R⁶⁰ through R⁶⁶ andmoderate base are as defined and X is halogen, preferably chlorine, C₁-C₄ alkyl--C(O)--O--, C₁ -C₄ alkoxy--C(O)--O-- or ##STR71## wherein R⁶⁰,R⁶⁵ and R⁶⁶ in this portion of the molecule are identical with those inthe reactant shown above and the moderate base is as defined, preferablytri-C₁ -C₆ alkylamine, alkali metal carbonate or alkali metal phosphate.

Generally, in step (1) mole amounts of the trione and substitutedbenzoyl reactant are used, along with a mole amount or excess of thebase. The two reactants are combined in an organic solvent such asmethylene chloride, toluene, ethyl acetate or dimethylformamide. Thebase or benzoyl reactant preferably is added to the reaction mixturewith cooling. The mixture is stirred at 0° C.-50° C. until the reactionis substantially complete. ##STR72## wherein the moderate base and R⁶⁰through R⁶⁶ are as defined above.

Generally, in step (2) a mole of the enol ester intermediate is reactedwith 1 to 4 moles of the moderate base, preferably about 2 moles ofmoderate base and from 0.01 mole to about 0.5 mole or higher, preferablyabout 0.1 mole of the cyanide source (e.g., potassium cyanide or acetonecyanohydrin). The mixture is stirred in a reaction pot until therearrangement is substantially complete at a temperature below 50° C.,preferably about 20° C. to about 40° C., and the desired product isrecovered by conventional techniques.

The term "cyanide source" refers to a substance or substances whichunder the rearrangement conditions consists of or generates hydrogencyanide and/or cyanide anion.

The process is conducted in the presence of a catalytic amount of asource of cyanide anion and/or hydrogen cyanide, together with a molarexcess, with respect to the enol ester, of a moderate base.

Preferred cyanide sources are alkali metal cyanides such as sodium andpotassium cyanide; cyanohydrins of methyl alkyl ketones having from 1-4carbon atoms in the alkyl groups, such as acetone or methyl isobutylketone cyanohydrins; cyanohydrins of benzaldehyde or of C₂ -C₅ aliphaticaldehydes such as acetaldehyde, propionaldehyde, etc., cyanohydrins;zinc cyanide; tri(lower alkyl) silyl cyanides, notably trimethyl silylcyanide; and hydrogen cyanide itself. Hydrogen cyanide is consideredmost advantageous as it produces relatively rapid reaction and isinexpensive. Among cyanohydrins the preferred cyanide source is acetonecyanohydrin.

The cyanide source is used in an amount up to about 50 mole percentbased on the enol ester. It may be used in as little as about 1 molepercent to produce an acceptable rate of reaction at about 40° C. on asmall scale. Larger scale reactions give more reproducible results withslightly higher catalyst levels of about 2 mole percent. Generally about1-10 mole % of the cyanide source is preferred.

The process is conducted with a molar excess, with respect to the enolester, of a moderate base. By the term "moderate base" is meant asubstance which acts as a base yet whose strength or activity as a baselies between that of strong bases such as hydroxides (which could causehydrolysis of the enol ester) and that of weak bases such asbicarbonates (which would not function effectively). Moderate basessuitable for use in this embodiment include both organic bases, e.g.,trialkylamines such as triethylamine and inorganic bases such as alkalimetal carbonates and phosphates. Suitable inorganic bases includepotassium carbonate and trisodium phosphate.

The base is used in an amount of from about 1 to about 4 moles per moleof enol ester, preferably about 2 moles per mole.

When the cyanide source is an alkali metal cyanide, particularlypotassium cyanide, a phase transfer catalyst may be included in thereaction. Particularly suitable phase transfer catalysts are the crownethers.

A number of different solvents are useful in this process, depending onthe nature of the acid halide or the acylated product. A preferredsolvent for this reaction is 1,2-dichloroethane. Other solvents whichmay be employed, depending on the reactants or products include toluene,acetonitrile, methylene chloride, ethyl acetate, dimethylformamide, andmethyl isobutyl ketone (MIBK).

In general, depending on the nature of the reactants and the cyanidesource, the rearrangement may be conducted at temperatures up to about50° C.

The above described substituted benzoyl chlorides can be prepared fromthe corresponding substituted benzoic acids according to the teaching ofReagents for Organic Synthesis, Vol. I, L. F. Fieser and M. Fieser, pp.767-769 (1967). ##STR73## wherein R⁶⁰, R⁶⁵ and R⁶⁶ are as previouslydefined.

The substituted benzoic acids can be prepared by a wide variety ofgeneral methods according to the teaching of The Chemistry of CarboxylicAcids and Esters, S. Patai, editor, J. Wiley and Sons, New York, N.Y.(1969) and Survey of Organic Synthesis, C. A. Buehler and D. F. Pearson,J. Wiley and Sons, (1970).

The following are three representative examples of the methods describedtherein. ##STR74## wherein R⁶⁰, R⁶⁵ and R⁶⁶ are as previously defined.

In reaction (a) the substituted benzonitrile is heated to reflux inaqueous sulfuric acid for several hours. The mixture is cooled and thereaction product is isolated by conventional techniques. ##STR75##wherein R⁶⁰, R⁶⁵ and R⁶⁶ are as previously defined.

In reaction (b) the substituted acetophenone is heated to reflux forseveral hours in an aqueous hypochlorite solution. The mixture is cooledand the reaction product is isolated by conventional techniques.##STR76## wherein R⁶⁰, R⁶⁵ and R⁶⁶ are as previously defined.

In reaction (c) the substituted toluene is heated to reflux in anaqueous solution of potassium permanganate for several hours. Thesolution is then filtered and the reaction product is isolated byconventional techniques.

The following example teaches the synthesis of a representative compoundof Embodiment G and G' of this invention.

EXAMPLE 1-G,G'2-(2'-Nitro-4'-chlorobenzoyl)-4,4,6,6-tetramethyl-1,3,5-cyclohexanetrione##STR77##

2-Nitro-4-chlorobenzoyl chloride (2.2 g, 10 mmol) and4,4,6,6-tetramethyl-1,3,5-cyclohexanetrione (1.8 g, 10 mmol) weredissolved in methylene chloride. Triethylamine was added and theresulting solution stirred at room temperature for 30 minutes. Thesolution was washed with 1 normal hydrochloric acid (1N HCl), andsaturated sodium chloride (brine), dried over anhydrous magnesiumsulfate (MgSO₄) and concentrated under vacuum. The residue was dissolvedin 20 ml acetonitrile. Triethylamine (5 ml, 3.5 equivalents) and acetonecyanohydrin (0.5 g, 0.6 equivalent) were added and the mixture stirredat room temperature for 4 hours. After dilution with ether, the solutionwas washed with 1N HCl and extracted with 5% K₂ CO₃. The basic extractwas acidified with HCl and extracted with ether. The ether extract waswashed with brine, dried over MgSO₄ and concentrated under vacuum,yielding 2.2 g of crude product. This was recrystallized from benzene toremove syncarpic acid still present. Concentration of the mother liquorunder vacuum gave 1.7 g of the desired product as an oil, whichsolidified on standing (m.p. 76°-82° C.). It was identified as such bynuclear magnetic resonance spectroscopy, infrared spectroscopy and massspectroscopy.

The following are tables of certain selected compounds of EmbodimentsA-G' that are preparable according to the procedures described herein.Compound numbers are assigned to each compound and are used throughoutthe remainder of the application.

                                      TABLE I-A                                   __________________________________________________________________________     ##STR78##                                                                    Cmpd.                                        n.sub.D.sup.30 or                No. R         R.sup.1                                                                          R.sup.2                                                                           R.sup.3    R.sup.4 R.sup.5                                                                            m.p. °C.                  __________________________________________________________________________     1A CH.sub.3  CH.sub.3                                                                         Cl  H          H       H    1.5613                            2A CH.sub.3  CH.sub.3                                                                         Cl  H          4-Cl    H    1.5655                            3A CH.sub.3  CH.sub.3                                                                         Cl  H          H       6-Cl 103-108                           4A*                                                                              H         H  Cl  H          4-Cl    H    138-140                           5A CH.sub.3  CH.sub.3                                                                         Br  H          H       H                                      6A CH.sub.3  CH.sub.3                                                                         Cl  H          H       5-Cl 74-77                             7A H         H  Cl  H          H       5-Cl 104-107                           8A H         H  Br  H          H       H    93-96                             9A H         H  Cl  H          H       H    79-87                             10A                                                                              H         H  I   H          H       H    66-70                             11A                                                                              H         H  Cl  H          4-NO.sub.2                                                                            H    118-122                           12A                                                                              H         H  Cl  H          H       6-Cl 143-148                           13A                                                                              H         H  Cl  H          H       5-Br 109-115                           14A                                                                              H         H  I   3-I        H       5-I  164-167                           15A                                                                              H         H  Cl  H          H       5-CH.sub.3                                                                         60-65                             16A                                                                              H         H  Cl  H          4-CH.sub.3                                                                            H    79-86                             17A                                                                              H         H  Cl  H          4-CH.sub.3 O                                                                          H    60-63                             18A                                                                              H         H  Cl  3-Cl       H       6-Cl                                   19A                                                                              H         H  Cl  H          H       5-CH.sub.3 O                                                                       77-80                             20A                                                                              H         H  Cl  3-Cl       H       H    80-90                             21A                                                                              H         H  Cl  H          H       5-CF.sub.3                                                                         74-75                             22A                                                                              H         H  Cl  H          H       5-NO.sub.2                                                                         140-143                           23A                                                                              H         H  Cl  3-Cl       4-Cl    H    152-154                           24A                                                                              H         H  Cl  3-Cl       4-CH.sub.3 O                                                                          H    169-170                           25A                                                                              H         H  Cl  H          4-Br    H    104-107                           26A                                                                              CH.sub.3  CH.sub.3                                                                         CH.sub.3 O                                                                        H          H       H    104-108                           27A                                                                              H         H  Cl  H                                                                                         ##STR79##                                                                            H                                      28A                                                                              H         H  Br  H          H       .sup.(a)                               29A                                                                              H         H  CH.sub.3 O                                                                        3-CH.sub.3 O                                                                             H       H    75-79                             30A                                                                              H         H  CH.sub.3 O                                                                        H          H       5-CH.sub.3 O                                                                       89-92                             31A                                                                              H         H  Br  H          4-CH.sub.3 O                                                                          5-CH.sub.3 O                                                                       92-96                             32A                                                                              H         H  Br  H          (4)-OCH.sub.2 O(5)                                                                         63-68                             33A                                                                              CH.sub.3  CH.sub.3                                                                         Cl  3-Cl       4-Cl    H    86-89                             34A                                                                              H         H  Cl  3-Cl       H       5-Cl                                   35A                                                                              CH.sub.3  CH.sub.3                                                                         Cl  3-Cl       H       5-Cl 105-109                           36A                                                                              CH.sub.3  CH.sub.3                                                                         Cl  3-Cl       4-Cl    5-Cl 137-139                           37A                                                                              H         H  Cl  3-Cl       4-Cl    5-Cl 106-110                           38A                                                                              H         H  Cl  H          4-Cl    5-Cl 108-111                           39A                                                                               ##STR80##                                                                              H  Cl  H          4-Cl    H                                      40A                                                                               ##STR81##                                                                              H  Cl  H          4-Cl    H                                      41A                                                                              CH(CH.sub.3).sub.2                                                                      H  Cl  H          4-Cl    H                                      42A                                                                              CH(CH.sub.3).sub.2                                                                      H  Cl  3-Cl       4-Cl    H                                      43A                                                                              H         H  Cl  H          4-F     H                                      44A                                                                              sodium salt of Compound No. 23           85-94                             45A                                                                              isopropylamine salt of Compound No. 23   160-165                           46A                                                                              triethylamine salt of Compound No. 23    82-85                             47A                                                                              potassium salt of Compound No. 23        107-106                           48A                                                                              triethanolammonium salt of Compound No. 39                                 49A                                                                              sodium salt of Compound No. 43           60-63                             50A                                                                              CH(CH.sub.3).sub.2                                                                      H  Cl  3-CH.sub.3 O                                                                             4-Br    H                                      51A                                                                              H         H  Cl  H          4-CH.sub.3 SO.sub.2                                                                   H    140-141                           52A                                                                              H         CH.sub.3                                                                         Cl  H          4-Cl    H                                      53A                                                                              i-C.sub.4 H.sub.9                                                                       H  Cl  H          4-Cl    H                                      54A                                                                              i-C.sub.3 H.sub.7                                                                       H  Cl  3-CH.sub.3 O                                                                             H       H                                      55A                                                                              CH.sub.3  CH.sub.3                                                                         Cl  H          4-CH.sub.3 SO.sub.2                                                                   H                                      56A                                                                              CH.sub.3  CH.sub.3                                                                         Cl  3-CH.sub.3 4-Cl    H                                      57A                                                                              H         H  Cl  3-CH.sub.3 4-Cl    H    56-64                             58A                                                                              H         H  Cl  H          4-C.sub.2 H.sub.5 SO.sub.2                                                            H     98-102                           59A                                                                              H         H  Cl  3-Cl       4-C.sub.2 H.sub.5 SO.sub.2                                                            H     98-109                           60A                                                                              H         H  Cl  H          4-C.sub.3 H.sub.7 SO.sub.2                                                            H    semi-solid                        61A                                                                              H         H  Cl  3-CH.sub.3 O                                                                             4-CH.sub.3 SO.sub.2                                                                   H    48-59                             62A                                                                              CH.sub.3  CH.sub.3                                                                         Cl  H          4-n-C.sub.3 H.sub.7 SO.sub.2                                                          H    semi-solid                        63A                                                                              H         H  Cl  3-Cl       4-n-C.sub.3 H.sub.7 SO.sub.2                                                          H      145-148.5                       64A                                                                              H         H  Cl  3-C.sub.2 H.sub.5 S                                                                      4-C.sub.2 H.sub.5 SO.sub.2                                                            H    oil                               65A                                                                              CH.sub.3  CH.sub.3                                                                         Cl  H          4-C.sub.2 H.sub.5 SO.sub.2                                                            H    103-108                           66A                                                                              CH.sub.3  CH.sub.3                                                                         Cl  3-Cl       4-C.sub.2 H.sub.5 SO.sub.2                                                            H    108-114                           67A                                                                              i-C.sub.3 H.sub.7                                                                       H  Cl  H          4-C.sub.2 H.sub.5 SO.sub.2                                                            H    brown gum                         68A                                                                              H         H  Cl  3-Cl       4-CH.sub.3 SO.sub.2                                                                   H    145-154                           69A                                                                              i-C.sub.3 H.sub.7                                                                       H  Cl  3-Cl       4-CH.sub.3 SO.sub.2                                                                   H                                      70A                                                                              H         H  Br  H          4-CH.sub.3 SO.sub.2                                                                   H    brown gum                         71A                                                                              H         H  Cl  H          4-i-C.sub.3 H.sub.7 SO.sub.2                                                          H    semi-solid                        72A                                                                              H         H  Cl  H          4-CH.sub.3 S                                                                          H    74-77                             73A                                                                              H         H  Cl  3-Cl       4-CH.sub.3 S                                                                          H                                      74A                                                                              CH.sub.3  CH.sub.3                                                                         Cl  3-Cl       4-n-C.sub.3 H.sub.7 SO.sub.2                                                          H    120-123                           75A                                                                              H         H  Cl  H          4-n-C.sub.4 H.sub.9 SO.sub.2                                                          H    semi-solid                        76A                                                                              CH.sub.3  CH.sub.3                                                                         Cl  H          4-n-C.sub.4 H.sub.9 SO.sub.2                                                          H                                      77A                                                                              H         H  Cl  3-C.sub.2 H.sub.5 O                                                                      4-CH.sub.3 SO.sub.2                                                                   H    semi-solid                        78A                                                                              H         H  Cl  3-CH.sub.3 O                                                                             4-n-C.sub.3 H.sub.7 SO.sub.2                                                          H    golden gum                        79A                                                                              CH.sub.3  CH.sub.3                                                                         Cl  H          4-i-C.sub.3 H.sub.7 SO.sub.2                                                          H    125-128                           80A                                                                              CH(CH.sub.3).sub.2                                                                      H  CH.sub.3 O                                                                        3-Cl       5-Cl    H                                      81A                                                                              H         H  Cl  3-CH.sub.3 O                                                                             4-Br    H    101-111                           82A                                                                              H         H  Cl  3-CH.sub.3 4-Cl    H    56-64                             83A                                                                              H         H  Cl  H          4-Cl    5-CH.sub.3 O                                                                       softens >70                       84A                                                                              CH(CH.sub.3).sub.2                                                                      H  Cl  3-n-C.sub.3 H.sub.7 O                                                                    4-Br    H                                      85A                                                                              H         H  Cl  3-C.sub.2 H.sub.5 O                                                                      4-Br    H    101-104                           86A                                                                              H         H  Cl  H          4-i-C.sub.4 H.sub.9 SO.sub.2                                                          H    136-140                           87A                                                                              CH.sub.3  CH.sub.3                                                                         Cl  H          4-i-C.sub.4 H.sub.9 SO.sub.2                                                          H                                      88A                                                                              H         H  Cl  3-Cl       4-i-C.sub.3 H.sub.7 SO.sub.2                                                          H    173-176                           89A                                                                              H         H  Cl  3-Cl       4-n-C.sub.4 H.sub.9 SO.sub.2                                                          H    135-138                           90A                                                                              H         H  Cl  3-C.sub.2 H.sub.5 O                                                                      4-C.sub.2 H.sub.5 SO.sub.2                                                            H    gum                               91A                                                                              H         H  Cl  3-CH.sub.3 O                                                                             4-C.sub.2 H.sub.5 SO.sub.2                                                            H    gum                               92A                                                                              H         H  Cl  3-Cl       4-C.sub.2 H.sub.5 S                                                                   H    91-94                             93A                                                                              H         H  Cl  3-C.sub.2 H.sub.5 S                                                                      4-n-C.sub.3 H.sub.7 SO.sub.2                                                          H    oil                               94A                                                                              H         H  Cl  3-C.sub.2 H.sub.5 S                                                                      4-C.sub.2 H.sub.5 S                                                                   H    oil                               95A                                                                              H         H  Cl  H          4-(CH.sub.3).sub.2 NSO.sub.2                                                          H    oil                               96A                                                                              H         H  Cl  3-C.sub.2 H.sub.5 O                                                                      4-n-C.sub.3 H.sub.7 SO.sub.2                                                          H                                      97A                                                                              H         H  Cl  3-n-C.sub.3 H.sub.7 O                                                                    4-C.sub.2 H.sub.5 SO.sub.2                                                            H    oil                               98A                                                                              CH.sub.3  CH.sub.3                                                                         Cl  H          4-(CH.sub.3).sub.2 NSO.sub.                                                           H    oil                               99A                                                                              H         H  Cl  H          4-(C.sub.2 H.sub.5).sub.2 NSO.sub.2                                                   H    90-92                            100A                                                                              CH.sub.3  CH.sub.3                                                                         Cl  H          4-(C.sub.2 H.sub.5).sub.2 NSO.sub.2                                                   H                                     101A                                                                              H         H  Cl  H          4-C.sub.2 H.sub.5 S                                                                   H                                     102A                                                                              H         H  Cl  H          4-n-C.sub.3 H.sub.7 S                                                                 H                                     103A                                                                              H         H  Cl  H          4-i-C.sub.3 H.sub.7 S                                                                 H                                     104A                                                                              H         H  Cl  H          4-C.sub.2 H.sub.5 SO                                                                  H                                     105A                                                                              H         H  CH.sub.3 O                                                                        H          4-NO.sub.2                                                                            H    semi-solid                       106A                                                                              H         H  Cl  3-n-C.sub.3 H.sub.7 O                                                                    4-Br    H                                     107A                                                                              H         H  Cl  3-n-C.sub.3 H.sub.7 O                                                                    4-CH.sub.3 SO.sub.2                                                                   H     96-100                          108A                                                                              H         H  Cl  3-allyloxy 4-CH.sub.3 SO.sub.2                                                                   H    semi-solid                       109A                                                                              H         H  Cl  3-CH.sub.3 C(O)NH                                                                        4-Cl    H    155-160                          110A                                                                              H         H  Cl  3-Cl       4-n-C.sub.3 H.sub.7 S                                                                 H                                     111A                                                                              H         H  Cl  3-CH.sub.3 O                                                                             4-NO.sub.2                                                                            H    150-153                          112A                                                                              H         H  Cl  3-allyloxy 4-C.sub.2 H.sub.5 SO.sub.2                                                            H                                     113A                                                                              H         H  Cl  3-CH.sub.2 BrCHBrCH.sub.2 O                                                              4-C.sub.2 H.sub.5 SO.sub.2                                                            H                                     114A                                                                              H         H  Cl  3-n-C.sub.4 H.sub.9 O                                                                    4-C.sub.2 H.sub.5 SO.sub.2                                                            H    gum                              115A                                                                              H         H  Cl  3-i-C.sub.4 H.sub.9 O                                                                    4-C.sub.2 H.sub.5 SO.sub.2                                                            H                                     116A                                                                              H         H  Cl  H          4-allylthio                                                                           H                                     117A                                                                              CH.sub.3  CH.sub.3                                                                         Cl  H          4-NO.sub.2                                                                            H                                     118A                                                                              H         H  Cl  3-CH.sub.3 C(O)N(CH.sub.3)                                                               4-Cl    H                                     119A                                                                              H         H  Cl  3-i-C.sub.3 H.sub.7 O                                                                    4-C.sub.2 H.sub.5 SO.sub.2                                                            H                                     120A                                                                              H         H  Cl  3-CH.sub.2 ClCH.sub.2 CH.sub.2 O                                                         4-C.sub.2 H.sub.5 SO.sub.2                                                            H    gum                              121A                                                                              H         H  Cl  H          4-t-C.sub.4 H.sub.9 S                                                                 H                                     122A                                                                              H         H  Cl  3-CH.sub.3 O                                                                             4-C.sub.2 H.sub.5 S                                                                   H                                     123A                                                                              H         H  Cl  H          4-CF.sub.3                                                                            H                                     124A                                                                              H         H  Cl  H          4-Cl    6-Cl                                  125A                                                                              H         H  Cl  3-CH.sub.3 C(O)N(CH.sub.3)                                                               H       H    131-135                          126A                                                                              H         H  Cl  3-CH.sub.3 C(O)NH                                                                        H       H                                     127A                                                                              H         H  Cl  3-(CH.sub.3).sub.2 N                                                                     4-Cl    H                                     128A                                                                              CH.sub.3  H  Cl  3-CH.sub.3 O                                                                             4-CH.sub.3 SO.sub.2                                                                   H    117-122                          129A                                                                              H         H  Cl  H          4-C.sub.2 H.sub.5 SO.sub.2                                                            H                                     130A                                                                              H         H  Br  H          H       H                                     131A                                                                              H         H  Br  H          4-C.sub.2 H.sub.5 OC(O)                                                               H                                     132A                                                                              H         H  Cl  H          4-CN    H    183-184                          133A                                                                              H         H  Cl  3-CH.sub.3 C(O)NH                                                                        H       6-NO.sub.2                            134A                                                                              H         H  Cl  3-(CH.sub.3).sub.2 N                                                                     H       H                                     135A                                                                              H         H  Cl  3-Cl       4-ClCH.sub.2 CH.sub.2 SO.sub.2                                                        H                                     __________________________________________________________________________     *Prepared in Example 1A.                                                      ##STR82##                                                                

                                      TABLE I-B                                   __________________________________________________________________________     ##STR83##                                                                    Compound                                                                      Number                                                                              R.sup.10 R.sup.11                                                                          R.sup.12                                                                          R.sup.13                                                                            R.sup.14  R.sup.15                                                                         R.sup.16                                                                         R.sup.17                                                                         R.sup.18                      __________________________________________________________________________     1B                                                                                  ##STR84##                                                                             H   Cl  H     4-Cl      H  H  H  H                              2B                                                                                  ##STR85##                                                                             CH.sub.3                                                                          Cl  H     4-Cl      H  H  H  H                              3B   triethanolammonium salt of Compound No. 2                                4B   triethanolammonium salt of Compound No. 7                                5B                                                                                  ##STR86##                                                                             CH.sub.3                                                                          Cl  3-Cl  4-Cl      H  H  H  H                              6B   triethanolammonium salt of Compound No. 5                                7B.sup.(a)                                                                         CH.sub.3 CH.sub.3                                                                          Cl  H     4-Cl      H  H  H  H                              8B   CH.sub.3 CH.sub.3                                                                          Cl  H     4-Cl      CH.sub.3                                                                         H  H  H                              9B   CH.sub.3 n-C.sub.3 H.sub.7                                                                 Cl  H     4-Cl      H  H  H  H                              10B  CH.sub.3 H   Cl  H     4-Cl      H  H  H  H                              11B  CH.sub.3 H   Cl  H     4-Cl      CH.sub.3                                                                         H  H  H                              12B  C.sub.5 H.sub.10                                                                           Cl  H     4-Cl      H  H  H  H                              13B  CH.sub.3 CH.sub.3                                                                          Cl  3-Cl  4-Cl      H  H  H  H                              14B  CH.sub.3 CH.sub.3                                                                          Cl  3-Cl  4-Cl      CH.sub.3                                                                         H  H  H                              15B  i-C.sub.3 H.sub.7                                                                      H   Cl  3-Cl  4-Cl      H  H  H  H                              16B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-CH.sub.3 SO.sub.2                                                                     H  H  H  H                              17B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-CH.sub.3 SO.sub.2                                                                     CH.sub.3                                                                         H  H  H                              18B  CH.sub.3 H   Cl  H     4-CH.sub.3 SO.sub.2                                                                     H  H  H  H                              19B  CH.sub.3 CH.sub.3                                                                          Cl  3-Cl  4-CH.sub.3 SO.sub.2                                                                     H  H  H  H                              20B  CH.sub.3 CH.sub.3                                                                          Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                              H  H  H  H                              21B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                              H  H  H  H                              22B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-C.sub.2 H.sub.5 SO.sub.2                                                              CH.sub.3                                                                         H  H  H                              23B  CH.sub.3 CH.sub.3                                                                          Cl  3-OCH.sub.3                                                                         4-C.sub.2 H.sub.5 SO.sub.2                                                              H  H  H  H                              24B  CH.sub.3 CH.sub.3                                                                          Cl  3-OCH.sub.3                                                                         4-CH.sub.3 SO.sub.2                                                                     H  H  H  H                              25B  CH.sub.3 CH.sub.3                                                                          Cl  3-CH.sub.3                                                                          4-Cl      H  H  H  H                              26B  CH.sub.3 CH.sub.3                                                                          Cl  3-OCH.sub.3                                                                         4-Cl      H  H  H  H                              27B  CH.sub.3 C.sub.2 H.sub.5                                                                   Cl  H     4-Cl      H  H  H  H                              28B  CH.sub.3 CH.sub.3                                                                          Cl  H     H         H  H  H  H                              29B  CH.sub.3 CH.sub.3                                                                          Cl  3-OCH.sub.3                                                                         4-Br      H  H  H  H                              30B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-Br      H  H  H  H                              31B  CH.sub.3 C.sub.2 H.sub.5                                                                   Cl  3-Cl  4-Cl      H  H  H  H                              32B  n-C.sub.3 H.sub.7                                                                      H   Cl  H     4-Cl      H  H  H  H                              33B                                                                                 ##STR87##                                                                             n-C.sub.3 H.sub.7                                                                 Cl  H     4-Cl      H  H  H  H                              34B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-i-C.sub.3 H.sub.7 SO.sub.2                                                            H  H  H  H                              35B  CH.sub.3 CH.sub.3                                                                          Cl  3-i-C.sub.3 H.sub.7 O                                                               4-Br      H  H  H  H                              36B  CH.sub.3 CH.sub.3                                                                          Cl  H     6-F       H  H  H  H                              37B  i-C.sub.3 H.sub.7                                                                      H   Cl  3-Cl  4-Cl      H  H  H  H                              38B  CH.sub.3 CH.sub.3                                                                          Cl  3-OC.sub.2 H.sub.5                                                                  4-Br      CH.sub.3                                                                         H  H  H                              39B  i-C.sub. 3 H.sub.7 OC(O)                                                               H   Cl  H     4-Cl      H  H  H  H                              40B  C.sub.2 H.sub.5 OC(O)                                                                  n-C.sub.3 H.sub.7                                                                 Cl  H     4-Cl      H  H  H  H                              41B  C.sub.5 H.sub.10                                                                           Cl  H     4-Cl      H  H  H  H                              42B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-Cl      H  H  CH.sub.3                                                                         H                              43B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-n-C.sub.3 H.sub.7 SO.sub.2                                                            H  H  H  H                              44B  CH.sub.3 CH.sub.3                                                                          Cl  3-Cl  4-n-C.sub.3 H.sub.7 SO.sub.2                                                            H  H  H  H                              45B  CH.sub.3 CH.sub.3                                                                          CH.sub.3 O                                                                        3-CH.sub.3 O                                                                        H         H  H  H  H                              46B  CH.sub.3 CH.sub.3                                                                          CH.sub.3 O                                                                        H     4-Cl      H  H  H  H                              47B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-Br      CH.sub.3                                                                         H  H  H                              48B  CH.sub.3 CH.sub.3                                                                          Br  H     H         H  H  H  H                              49B  CH.sub.3 CH.sub.3                                                                          I   H     H         H  H  H  H                              50B  CH.sub.3 CH.sub.3                                                                          F   H     H         H  H  H  H                              51B  CH.sub.3 CH.sub.3                                                                          CH.sub.3 O                                                                        H     H         H  H  H  H                              52B  CH.sub.3 CH.sub. 3                                                                         Cl  3-allyloxy                                                                          4-Br      H  H  H  H                              53B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-CH.sub.3 SO.sub.2                                                                     H  H  CH.sub.3                                                                         H                              54B  CH.sub.3 CH.sub.3                                                                          Cl  3-CH.sub.3 O                                                                        4-Br      CH.sub.3                                                                         H  H  H                              55B  CH.sub.3 CH.sub.3                                                                          Br  H     4-CN      H  H  H  H                              56B  CH.sub.3 CH.sub.3                                                                          Cl  H     4N(CH.sub.3)SO.sub.2 CF.sub.3                                                           H  H  H  H                              57B  CH.sub.3 CH.sub.3                                                                          Cl  3-NO.sub.2                                                                          H         H  H  H  H                              58B  CH.sub.3 CH.sub.3                                                                          C.sub.2 H.sub.5 O                                                                 H     3-Cl      H  H  H  H                              59B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-i-C.sub.4 H.sub.9 SO.sub.2                                                            H  H  H  H                              60B  CH.sub.3 CH.sub.3                                                                          Cl  3-C.sub.2 H.sub.5 O                                                                 4-CH.sub.3 SO.sub.2                                                                     H  H  H  H                              61B  CH.sub.3 CH.sub.3                                                                          Cl  3-CH.sub.3 O                                                                        4-C.sub.2 H.sub.5 SO.sub.2                                                              H  H  H  H                              62B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-n-C.sub.4 H.sub.9 SO.sub.2                                                            H  H  H  H                              63B  CH.sub.3 CH.sub.3                                                                          Cl  3-Cl  4-n-C.sub.4 H.sub.9 SO.sub.2                                                            CH.sub.3                                                                         H  H  H                              64B  CH.sub.3 CH.sub.3                                                                          Cl  3-Cl  4-C.sub.2 H.sub.5 SO.sub.2                                                              CH.sub.3                                                                         H  H  H                              65B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-F       H  H  H  H                              66B  CH.sub.3 H   Cl  3-CH.sub.3 O                                                                        4-Br      H  H  H  H                              67B  CH.sub.3 CH.sub.3                                                                          Cl  3-CH.sub.3 O                                                                        H         H  H  H  H                              68B  CH.sub.3 CH.sub.3                                                                          Cl  3-C.sub.2 H.sub.5 S                                                                 4-n-C.sub.3 H.sub.7 SO.sub.2                                                            H  H  H  H                              69B  CH.sub.3 CH.sub.3                                                                          Cl  3-C.sub.2 H.sub.5 S                                                                 4-C.sub.2 H.sub.5 S                                                                     H  H  H  H                              70B  CH.sub.3 CH.sub.3                                                                          Cl  3-C.sub.2 H.sub.5 S                                                                 4-C.sub.2 H.sub.5 SO.sub.2                                                              H  H  H  H                              71B  CH.sub.3 CH.sub.3                                                                          Cl  3-C.sub.2 H.sub.5 S                                                                 4-CH.sub.3 SO.sub.2                                                                     H  H  H  H                              72B  CH.sub.3 CH.sub.3                                                                          Cl  Cl    4-i-C.sub.3 H.sub.7 SO.sub.2                                                            H  H  H  H                              73B  CH.sub.3 CH.sub.3                                                                          Cl  3-Cl  4-n-C.sub.4 H.sub.9 SO.sub.2                                                            H  H  H  H                              74B  CH.sub.3 CH.sub.3                                                                          Cl  3-C.sub.2 H.sub.5 O                                                                 4-C.sub.2 H.sub.5 SO.sub.2                                                              H  H  H  H                              75B  CH.sub.3 CH.sub.3                                                                          Cl  3-C.sub.2 H.sub.5 O                                                                 4-Br      H  H  H  H                              76B  CH.sub.3 CH.sub.3                                                                          Cl  3-C.sub.2 H.sub.5 O                                                                 4-n-C.sub.3 H.sub.7 SO.sub.2                                                            H  H  H  H                              77B  CH.sub.3 CH.sub.3                                                                          Cl  3-n-C.sub.3 H.sub.7 O                                                               4-C.sub.2 H.sub.5 SO.sub.2                                                              H  H  H  H                              78B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-(CH.sub.3).sub.2 NSO.sub.2                                                            H  H  H  H                              79B  CH.sub.3 CH.sub.3                                                                          Cl  3-CH.sub.3 S                                                                        4-C.sub.2 H.sub.5 SO.sub.2                                                              H  H  H  H                              80B  CH.sub.3 CH.sub.3                                                                          Cl  3-Cl  4-C.sub.2 H.sub.5 S                                                                     H  H  H  H                              81B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-C.sub.2 H.sub.5 S                                                                     H  H  H  H                              82B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-(C.sub.2 H.sub.5).sub.2 NSO.sub.2                                                     H  H  H  H                              83B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-n-C.sub.3 H.sub.7 SO.sub.2                                                            H  H  H  H                              84B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-n-C.sub.3 H.sub.7 S                                                                   CH.sub.3                                                                         H  H  H                              85B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-C.sub. 2 H.sub.5 S(O)                                                                 H  H  H  H                              86B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-i-C.sub.3 H.sub.7 S                                                                   H  H  H  H                              87B  CH.sub.3 CH.sub.3                                                                          Cl  3-Cl  4-n-C.sub.3 H.sub.7 S                                                                   H  H  H  H                              88B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-t-C.sub.4 H.sub.9 SO.sub.2                                                            H  H  H  H                              89B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-i-C.sub.3 H.sub.7 S                                                                   CH.sub.3                                                                         H  H  H                              90B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-n-C.sub.3 H.sub.7 SO.sub.2                                                            CH.sub.3                                                                         H  H  H                              91B  CH.sub.3 CH.sub.3                                                                          CL  *     4-Cl      H  H  H  H                              92B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-CH.sub.2CHCH.sub.2 S                                                                  H  H  H  H                              93B  CH.sub.3 CH.sub.3                                                                          Cl  3-C.sub.2 H.sub.5 O                                                                 4-C.sub.2 H.sub.5 S                                                                     H  H  H  H                              94B  CH.sub.3 CH.sub.3                                                                          Cl  3-Cl  4-CH.sub.3 S                                                                            CH.sub.3                                                                         H  H  H                              95B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-CH.sub.3 S                                                                            H  H  H  H                              96B  CH.sub.3 CH.sub.3                                                                          Cl  3-i-C.sub.3 H.sub.7 O                                                               4-C.sub.2 H.sub.5 SO.sub.2                                                              H  H  H  H                              97B  CH.sub.3 CH.sub.3                                                                          Cl  3-CH.sub.3 O                                                                        4-C.sub.2 H.sub.5 S                                                                     H  H  H  H                              98B  CH.sub.3 CH.sub.3                                                                          Cl  **    4-Cl      H  H  H  H                              99B  CH.sub.3 CH.sub.3                                                                          Cl  **    H         H  H  H  H                             100B  CH.sub.3 CH.sub.3                                                                          Cl  3-Cl  4-CH.sub.3 S                                                                            H  H  H  H                             101B  CH.sub.3 CH.sub.3                                                                          CH.sub.3 O                                                                        H     4-NO.sub.2                                                                              H  H  H  H                             102B  CH.sub.3 CH.sub.3                                                                          CH.sub.3 O                                                                        H     4-CF.sub.3                                                                              H  H  H  H                             103B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-n-C.sub.3 H.sub.7 SO                                                                  H  H  H  H                             104B  CH.sub.3 CH.sub.3                                                                          Cl  H     4-n-C.sub.3 H.sub.7 SO                                                                  CH.sub.3                                                                         H  H  H                             __________________________________________________________________________     .sup.(a) Prepared in Example IB.                                              *3-CH.sub.3 C(O)NH                                                            **3-CH.sub.3 C(O)N(CH.sub.3)                                             

The following additional compounds can be prepared by the general methodhereinbefore taught.

                                      TABLE I-B                                   __________________________________________________________________________     ##STR88##                                                                    R.sup.10                                                                           R.sup.11                                                                           R.sup.12                                                                         R.sup.13                                                                             R.sup.14                                                                             R.sup.15                                                                         R.sup.16                                                                         R.sup.17                                                                         R.sup.18                                  __________________________________________________________________________    CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl H      4-Cl   CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl H      4-Cl   H  H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl H      4-Cl   CH.sub.3                                                                         H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl H      4-Cl   H  H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl H      4-Cl   CH.sub.3                                                                         H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl H      4-Cl   H  H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl H      4-Cl   CH.sub.3                                                                         H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl H      4-Cl   H  H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl H      4-Cl   CH.sub.3                                                                         H  H  H                                         C.sub.5 H.sub.10                                                                        Cl H      4-Cl   CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-Cl   4-Cl   H  H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-Cl   4-Cl   CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-Cl   4-Cl   H  H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-Cl   4-Cl   CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           H    Cl 3-Cl   4-Cl   H  H  H  H                                         CH.sub.3                                                                           H    Cl 3-Cl   4-Cl   CH.sub.3                                                                         H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-Cl   4-Cl   H  H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-Cl   4-Cl   CH.sub.3                                                                         H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-Cl   4-Cl   H  H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-Cl   4-Cl   CH.sub.3                                                                         H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-Cl   4-Cl   H  H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-Cl   4-Cl   CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl H      4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl H      4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl H      4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl H      4-CH.sub.2 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           H    Cl H      4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl H      4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl H      4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl H      4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl H      4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl H      4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl H      4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         C.sub.5 H.sub.10                                                                        Cl H      4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         C.sub.5 H.sub.10                                                                        Cl H      4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-Cl   4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-Cl   4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-Cl   4-CH.sub.2 SO.sub.2                                                                  H  H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-Cl   4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           H    Cl 3-Cl   4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         CH.sub.3                                                                           H    Cl 3-Cl   4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-Cl   4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-Cl   4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-Cl   4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-Cl   4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl 3-Cl   4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl 3-Cl   4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-Cl   4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-Cl   4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-Cl   4-.sub.2 H.sub.5 SO.sub.2                                                            H  H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           H    Cl 3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         CH.sub.3                                                                           H    Cl 3-Cl   4-C.sub.2 H.sub.5 SO.sub. 2                                                          CH.sub.3                                                                         H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl 3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         i-C.sub.2 H.sub.7                                                                  H    Cl 3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-Cl   4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl H      4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl H      4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl H      4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl H      4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           H    Cl H      4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         CH.sub.3                                                                           H    Cl H      4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl H      4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl H      4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl H      4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl H      4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl H      4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl H      4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         C.sub.5 H.sub.10                                                                        Cl H      4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         C.sub.5 H.sub.10                                                                        Cl H      4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           CH.sub.3                                                                           Cl 3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           H    Cl 3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         CH.sub.3                                                                           H    Cl 3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl 3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl 3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-OCH.sub.3                                                                          4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           CH.sub.3                                                                           Cl 3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         CH.sub.3                                                                           CH.sub.3                                                                           Cl 3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           H    Cl 3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         CH.sub.3                                                                           H    Cl 3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl 3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           H  H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl 3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-CH.sub.3                                                                           4-C.sub. 2 H.sub.5 SO.sub.2                                                          H  H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-CH.sub.3                                                                           4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           CH.sub.3                                                                           Cl 3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           H    Cl 3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         CH.sub.3                                                                           H    Cl 3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl 3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl 3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-OCH.sub.3                                                                          4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           CH.sub.3                                                                           Cl 3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         CH.sub.3                                                                           CH.sub.3                                                                           Cl 3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           H    Cl 3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         CH.sub.3                                                                           H    Cl 3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl 3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  H  H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl 3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                     H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-CH.sub.3                                                                           4-CH.sub.3 SO.sub.2                                                                  CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           CH.sub.3                                                                           Cl 3-CH.sub.3                                                                           4-Cl   CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-CH.sub.3                                                                           4-Cl   H  H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-CH.sub.3                                                                           4-Cl   CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-CH.sub.3                                                                           4-Cl   H  H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-CH.sub.3                                                                           4-Cl   CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           H    Cl 3-CH.sub.3                                                                           4-Cl   H  H  H  H                                         CH.sub.3                                                                           H    Cl 3-CH.sub.3                                                                           4-Cl   CH.sub.3                                                                         H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-CH.sub.3                                                                           4-Cl   H  H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-CH.sub.3                                                                           4-Cl   CH.sub.3                                                                         H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-CH.sub.3                                                                           4-Cl   H  H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-CH.sub.3                                                                           4-Cl   CH.sub.3                                                                         H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl 3-CH.sub.3                                                                           4-Cl   H  H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl 3-CH.sub.3                                                                           4-Cl   CH.sub.3                                                                         H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-CH.sub.3                                                                           4-Cl   H  H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-CH.sub.3                                                                           4-Cl   CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           CH.sub.3                                                                           Cl 3-OCH.sub.3                                                                          4-Cl   CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-OCH.sub.3                                                                          4-Cl   H  H  H  H                                         CH.sub.3                                                                           n-C.sub.3 H.sub.7                                                                  Cl 3-OCH.sub.3                                                                          4-Cl   CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-OCH.sub.3                                                                          4-Cl   H  H  H  H                                         CH.sub.3                                                                           n-C.sub.4 H.sub.9                                                                  Cl 3-OCH.sub.3                                                                          4-Cl   CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           H    Cl 3-OCH.sub.3                                                                          4-Cl   H  H  H  H                                         CH.sub.3                                                                           H    Cl 3-OCH.sub.3                                                                          4-Cl   CH.sub.3                                                                         H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-OCH.sub.3                                                                          4-Cl   H  H  H  H                                         C.sub.2 H.sub.5                                                                    H    Cl 3-OCH.sub.3                                                                          4-Cl   CH.sub.3                                                                         H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-OCH.sub.3                                                                          4-Cl   H  H  H  H                                         n-C.sub.4 H.sub.9                                                                  H    Cl 3-OCH.sub.3                                                                          4-Cl   CH.sub.3                                                                         H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl 3-OCH.sub.3                                                                          4-Cl   H  H  H  H                                         i-C.sub.3 H.sub.7                                                                  H    Cl 3-OCH.sub.3                                                                          4-Cl   CH.sub.3                                                                         H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-OCH.sub.3                                                                          4-Cl    H H  H  H                                         C.sub.5 H.sub.10                                                                        Cl 3-OCH.sub.3                                                                          4-Cl   CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           CH.sub.3                                                                           Cl 3-n-C.sub.3 H.sub.7 O                                                                4-Br   H  H  H  H                                         CH.sub.3                                                                           CH.sub.3                                                                           Cl H      4-C.sub.2 H.sub.5 SO.sub.2                                                           CH.sub.3                                                                         H  H  H                                         CH.sub.3                                                                           CH.sub.3                                                                           Cl H      4-NO.sub.2                                                                           H  H  H  H                                         CH.sub.3                                                                           CH.sub.3                                                                           Cl 3-C.sub.2 H.sub.5 O                                                                  4-CH.sub.3 S                                                                         H  H  H  H                                         CH.sub.3                                                                           CH.sub.3                                                                           Cl H      4-CN   H  H  H  H                                         CH.sub.3                                                                           CH.sub.3                                                                           Cl 3-(CH.sub.3).sub.2 N                                                                 4-Cl   H  H  H  H                                         __________________________________________________________________________

                                      TABLE I-C                                   __________________________________________________________________________     ##STR89##                                                                    Comp.                                                                         No. R.sup.21                                                                          R.sup.22                                                                          R.sup.23                                                                         R.sup.24                                                                         R.sup.25                                                                         R.sup.26                                                                         R.sup.27                                                                         R.sup.28                                                                          n.sub.D.sup.30 or m.p.                         __________________________________________________________________________    1C.sup.a                                                                          CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H  H  H   oil                                            2C  H   H   H  H  H  H  H  CN  124-140° C.                             __________________________________________________________________________     .sup.a Prepared in Example IC.                                           

                                      TABLE I-D                                   __________________________________________________________________________     ##STR90##                                                                    Comp.                                                                         No. R.sup.31                                                                         R.sup.32                                                                          R.sup.33                                                                          R.sup.34                                                                         R.sup.35                                                                         R.sup.36                                                                         R.sup.37                                                                            R.sup.38 n.sub.D.sup.30 or                      __________________________________________________________________________                                           m.p.                                   1D  CH.sub.3                                                                         H   H   H  H  H  H     H        viscous oil                            2D  CH.sub.3                                                                         CH.sub.3                                                                          H   H  CH.sub.3                                                                         H  H     H        viscous oil                            3D.sup.a                                                                          H  H   H   H  H  H  H     H        132-135                                4D  CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     H        viscous oil                            5D.sup.b                                                                          H  H   CH.sub.3                                                                          CH.sub.3                                                                         H  H  H     H        130-133                                6D  CH.sub.3                                                                         H   H   H  CH.sub.3                                                                         H  H     H        viscous oil                            7D  CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     CF.sub.3 52-61                                  8D  H  H   H   H  H  H  H     CF.sub.3 88-94                                  9D  H  H   CH.sub.3                                                                          CH.sub.3                                                                         H  H  H     CF.sub.3 89-97                                  10D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  3-CH.sub.3                                                                          H        119-122                                11D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  3-Cl  H        72-79                                  12D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     Cl       118-121                                13D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  5-Cl  H        118-120                                14D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  5-F   H        130-133                                15D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  3-CH.sub.3 O                                                                        H        139-142                                16D CH.sub.3                                                                         CH.sub.3                                                                          CH.sub.3                                                                          H  H  H  H     CF.sub.3 viscous oil                            17D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     NO.sub.2 viscous oil                            18D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     Br       viscous oil                            19D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  CH.sub.3                                                                         5-CH.sub.3                                                                          H        viscous oil                            20D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  5-CH.sub.3                                                                          H        viscous oil                            21D H  H   H   H  H  H  H     F        123-128                                22D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     F        viscous oil                            23D H  H   H   H  H  H  H     Cl       viscous oil                            24D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     SO.sub.2 CH.sub.3                                                                      130-133                                25D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     SO.sub.2n-C.sub.3 H.sub.7                                                              viscous oil                            26D H  H   H   H  H  H  H     SO.sub.2 CH.sub.3                                                                      157-159                                27D H  H   H   H  H  H  H     SO.sub.2n-C.sub.3 H.sub.7                                                              120-123                                28D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  5-F   H        165-195                                29D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     SO.sub.2C.sub.2 H.sub.5                                                                oil                                    30D CH.sub.3                                                                         CH.sub.3                                                                          H   H  CH.sub.3                                                                         H  H     SO.sub.2CH.sub.3                                                                       gum                                    31D CH.sub.3                                                                         n-C.sub.4 H.sub.9                                                                 H   H  H  H  H     H        viscous oil                            32D H  H   i-C.sub.4 H.sub.9                                                                 H  H  H  H     H        viscous oil                            33D H  H   H   H  H  H  H     SO.sub.2C.sub.2 H.sub.5                                                                viscous oil                            34D H  H   H   H  H  H  H     CN       viscous oil                            35D H  H   H   H  H  H  H     SO.sub.2 N(CH.sub.3).sub.2                                                             158-159                                36D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     SO.sub.2 N(CH.sub.3).sub.2                                                             120-130                                37D H  H   H   H  H  H  H     SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                      158-163                                38D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                      oil                                    39D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H                                                                                    ##STR91##                                                                             oil                                    40D H  H   CH.sub.3                                                                          CH.sub.3                                                                         H  H  H     SO.sub.2N(C.sub.2 H.sub.5).sub.2                                                       oil                                    41D H  H   H   H  H  H  H     SC.sub.2 H.sub.5                                                                       oil                                    42D H  H   H   H  H  H  H     S(O)n-C.sub.3 H.sub.7                                                                  oil                                    43D H  H   H   H  H  H  H     Sn-C.sub.3 H.sub.7                                                                     oil                                    44D CH.sub.3                                                                         CH.sub.3                                                                          H   H  CH.sub.3                                                                         H  H     Sn-C.sub.3 H.sub.7                                                                     oil                                    45D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     Sn-C.sub.3 H.sub.7                                                                     oil                                    46D CH.sub.3                                                                         CH.sub.3                                                                          H   H  CH.sub.3                                                                         H  H     SC.sub.2 H.sub.5                                                                       oil                                    47D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     SC.sub.2 H.sub.5                                                                       oil                                    47D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     SC.sub.2 H.sub.5                                                                       oil                                    48D H  H   H   H  H  H  H     SCH.sub.3                                                                              94-97                                  49D CH.sub.3                                                                         CH.sub.3                                                                          H   H  CH.sub.3                                                                         H  H     CF.sub.3 oil                                    50D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     SCH.sub.3                                                                              oil                                    51D .sup.c                                                                           H   i-C.sub.3 H.sub.7                                                                 H  H  H  H     H        145-148                                52D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  5-CH.sub.3 O                                                                        Br       oil                                    53D H  H   CH.sub.3                                                                          CH.sub.3                                                                         H  H  H     Cl       oil                                    54D H  H   H   H  H  H  3-CH.sub.3 O                                                                        Cl       oil                                    55D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  3-CH.sub.3 O                                                                        Cl       oil                                    56D CH.sub.3                                                                         CH.sub.3                                                                          H   H  CH.sub.3                                                                         H  H     CH.sub.3 S                                                                             oil                                    57D H  H   H   H  H  H  H                                                                                    ##STR92##                                                                             120-125                                58D H  H   CH.sub.3                                                                          CH.sub.3                                                                         H  H  H     CN       175-177                                59D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     CN       151-153                                60D CH.sub.3                                                                         CH.sub.3                                                                          H   H  CH.sub.3                                                                         H  H     CN       oil                                    61D .sup.c                                                                           H   H   H  H  H  H     H        oil                                    62D .sup.d                                                                           H   H   H  H  H  H     H        oil                                    63D H  H   CH.sub.3                                                                          H  H  H  H     Cl       110-115                                64D H  H   CH.sub.3                                                                          H  H  H  H     SO.sub.2n-C.sub.3 H.sub.7                                                              oil                                    65D .sup.d                                                                           CH.sub.3                                                                          H   H  H  H  H     Cl       oil                                    66D H  H   H   H  H  H  H     SO.sub.2 CHCl.sub.2                                                                    oil                                    67D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     SO.sub.2 CHCl.sub.2                                                                    oil                                    68D H  H   H   H  H  H  .sup.c                                                                              Br       oil                                    69D H  H   H   H  H  H  H     SO.sub.2 CH.sub.2 Cl                                                                   oil                                    70D CH.sub.3                                                                         CH.sub.3                                                                          H   H  H  H  H     SO.sub.2 CH.sub.2 Cl                                                                   wax                                    71D .sup.d                                                                           CH.sub.3                                                                          H   H  H  H  H     H        oil                                    72D H  H   H   H  H  H  C.sub.2 H.sub.5 O                                                                   Cl       oil                                    73D CH.sub.3                                                                         CH.sub.3                                                                          H   H  CH.sub.3                                                                         H  CH.sub.3 O                                                                          CF.sub.3 oil                                    __________________________________________________________________________     .sup.a Prepared in Example 1D,D'.                                             .sup.b Prepared in Example 2D,D'.                                             .sup.c C.sub.2 H.sub.5 OC(O)-                                                 .sup.d i-C.sub.3 H.sub.7 OC(O)-                                          

                                      TABLE I-E                                   __________________________________________________________________________     ##STR93##                                                                    Comp.                                                                         No. n R.sup.40                                                                         R.sup.41                                                                         R.sup.42                                                                         R.sup.43                                                                         R.sup.44                                                                         R.sup.45                                                                         R.sup.46                                                                         R.sup.47                                                                          R.sup.48                                                                              m.p.                                   __________________________________________________________________________    1E  0 CH.sub.3                                                                         H  H  H  H  H  H  H   H       79-81° C.                       2E  0 CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H  H  H  H  H   H       oil                                    3E.sup.a                                                                          0 CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H  H  CH.sub.3                                                                         H  H   H       oil                                    4E.sup.b                                                                          2 CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H  H  CH.sub.3                                                                         H  H   H       oil                                    5E  0 C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         CH.sub.3                                                                         H  H  H  H  H   H       oil                                    6E  2 C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         CH.sub.3                                                                         H  H  H  H  H   H       oil                                    7E  0 CH.sub.3                                                                         H  H  H  H  H  H  3-Cl                                                                              Cl      59-64° C.                       8E  2 CH.sub.3                                                                         H  H  H  H  H  H  3-Cl                                                                              Cl      116-119° C.                     9E  0 CH.sub.3                                                                         H  H  H  H  H  H  H   CF.sub.3                                                                              102-106° C.                     10E 2 CH.sub.3                                                                         H  H  H  H  H  H  H   CF.sub.3                                                                              oil                                    11E 0 CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H  H  H  H  H   CF.sub.3                                                                              49-53° C.                       12E 2 CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H  H  H  H  H   CF.sub.3                                                                              oil                                    13E.sup.c                                                                         1 CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H  H  H  H  H   CF.sub.3                                                                              oil                                    14E 0 CH.sub.3                                                                         H  H  H  H  H  H  3-Cl                                                                              SCH.sub.3                                                                             105-107° C.                     15E 1 CH.sub.3                                                                         H  H  H  H  H  H  3-Cl                                                                              S(O)CH.sub.3                                                                          oil                                    16E 0 CH.sub.3                                                                         H  H  H  H  H  H  H   SO.sub.2 n-C.sub.3 H.sub.7                                                            oil                                    17E 0 CH.sub.3                                                                         H  H  H  H  H  H  H   SCH.sub.3                                                                             101-103° C.                     18E 2 CH.sub.3                                                                         H  H  H  H  H  H  H   SO.sub.2 n-C.sub.3 H.sub.7                                                            oil                                    19E 2 CH.sub.3                                                                         H  H  H  H  H  H  H   SO.sub.2 CH.sub.3                                                                     194-196° C.                     20E 0 CH.sub.3                                                                         H  H  H  H  H  H  3-CH.sub.3                                                                        H       40-42° C.                       21E 2 CH.sub.3                                                                         H  H  H  H  H  H  3-CH.sub.3                                                                        H       80-86° C.                       __________________________________________________________________________     .sup.a Prepared in Example 1E,E'.                                             .sup.b Prepared in Example 2E,E'.                                             .sup.c Prepared in Example 3E,E'.                                        

                                      TABLE I-F                                   __________________________________________________________________________     ##STR94##                                                                    Comp.                                  n.sub.D.sup.30                         No. R.sup.50                                                                         R.sup.51                                                                         R.sup.52                                                                         R.sup.53                                                                          R.sup.54                                                                          R.sup.55                                                                         R.sup.56                                                                         R.sup.57                                                                          R.sup.58                                                                              or m.p.                                __________________________________________________________________________    1F  CH.sub.3                                                                         H  H  H   H   H  H  H   H       35-42° C.                       2F  CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   H       47-53° C.                       3F  CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   Br      oil                                    4F  CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   CN      oil                                    5F  CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  3-NO.sub.2                                                                        H       oil                                    6F  CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  5-Cl                                                                              H       oil                                    7F  CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   CH.sub.3 SO.sub.2                                                                     oil                                    8F  CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                         H  H   CH.sub.3 SO.sub.2                                                                     oil                                    9F  CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  3-Cl                                                                              H       oil                                    10F CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                         H  H   C.sub.2 H.sub.5 SO.sub.2                                                              oil                                    11F CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   C.sub.2 H.sub.5 SO.sub.2                                                              oil                                    12F CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   n-C.sub.3 H.sub.7 SO.sub.2                                                            oil                                    13F CH.sub.3                                                                         H  H  H   H   H  H  H   CH.sub.3 SO.sub.2                                                                     oil                                    14F CH.sub.3                                                                         H  H  H   H   H  H  H   n-C.sub.3 H.sub.7 SO.sub.2                                                            oil                                    15F CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   CH.sub.3 S                                                                            oil                                    16F C.sub.2 H.sub.5                                                                  CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   Br      oil                                    17F CH.sub.3                                                                         H  H  H   H   H  H  H   CN      oil                                    18F CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   F       oil                                    19F CH.sub.3                                                                         H  H  H   H   H  H  H   C.sub.2 H.sub.5SO.sub.2                                                               oil                                    20F CH.sub.3                                                                         H  H  H   H   H  H  3-Cl                                                                              H       65-67° C.                       21F CH.sub.3                                                                         H  H  H   H   H  H  3-I H       oil                                    22F CH.sub.3                                                                         H  H  H   H   H  H  3-NO.sub.2                                                                        H       oil                                    23F CH.sub.3                                                                         H  H  H   H   H  H  3-CN                                                                              H       96-101° C.                      24F CF.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   H       oil                                    25F CF.sub.3                                                                         H  H  H   H   H  H  H   H       oil                                    26F CF.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   Br      oil                                    27F CF.sub.3                                                                         H  H  H   H   H  H  H   Cl      82-88° C.                       28F CF.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   Cl      oil                                    29F CF.sub.3                                                                         H  H  H   H   H  H  H   C.sub.2 H.sub.5 S                                                                     oil                                    30F CF.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   C.sub.2 H.sub.5 SO.sub.2                                                              oil                                    31F CF.sub.3                                                                         H  H  H   H   H  H  H   CN      oil                                    32F CF.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   CN      oil                                    33F.sup.a                                                                         CF.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                         H  H   Br      oil                                    34F CH.sub.3                                                                         H  H  H   H   H  H  H   CH.sub.3                                       35F CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  3-Cl                                                                              C.sub.2 H.sub.5 SO.sub.2                                                              115-117° C.                     36F CH.sub.3                                                                         H  H  H   H   H  H  3-Cl                                                                              C.sub.2 H.sub.5 SO.sub.2                                                              oil                                    37F CH.sub.3                                                                         .sup.b                                                                           .sup.b                                                                           H   H   H  H  3-CF.sub.3                                                                        H       oil                                    38F CH.sub.3                                                                         .sup.c                                                                           H  i-C.sub.3 H.sub.7                                                                 H   H  H  3-NO.sub.2                                                                        H       88-108° C.                      39F CF.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                         H  H   CH.sub.3 S                                                                            oil                                    40F CF.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   CH.sub.3 S                                                                            oil                                    41F CF.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                         H  H   CH.sub.3 SO.sub.2                                                                     oil                                    42F CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   CF.sub.3                                                                              oil                                    43F CH.sub.3                                                                         H  H  H   H   H  H  H   CF.sub.3                                                                              114-120° C.                     44F CH.sub.3                                                                         H  H  H   H   H  H  3-Cl                                                                              Cl      oil                                    45F CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  3-Cl                                                                              Cl      oil                                    46F CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  3-CF.sub.3                                                                        H       oil                                    47F CF.sub.3                                                                         H  H  H   H   H  H  H   CH.sub.3 S                                                                            oil                                    48F CF.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                         H  H   CF.sub.3                                                                              oil                                    49F CF.sub.3                                                                         H  H  H   H   H  H  H   CF.sub.3                                                                              oil                                    50F CF.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   H  H  H   CF.sub.3                                                                              oil                                    51F CH.sub.3                                                                         H  H  CH.sub.3                                                                          H   H  H  H   CH.sub.3 SO.sub.2                                                                     oil                                    52F CF.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H   H   CH.sub.3                                                                         H  H   C.sub.2 H.sub.5 SO.sub.2                                                              oil                                    53F CH.sub.3                                                                         H  H  H   H   H  H  H   Br      94-98° C.                       54F CH.sub.3                                                                         H  H  H   H   H  H  .sup.d                                                                            H       oil                                    __________________________________________________________________________     .sup.a Prepared in Example 1F,F'.                                             .sup.b (CH.sub.2).sub.5                                                       .sup.c C.sub.2 H.sub.5 OC(O)-                                                 .sup. d 3-N(CH.sub.3)COCH.sub.3                                          

                                      TABLE I-G                                   __________________________________________________________________________     ##STR95##                                                                    Comp.                                                                         No. R.sup.60                                                                           R.sup.61                                                                         R.sup.62                                                                         R.sup.63                                                                         R.sup.64                                                                         R.sup.65                                                                           R.sup.66                                                                              m.p. °C.                             __________________________________________________________________________     1G NO.sub.2                                                                           CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    H       112-117                                      2G.sup.(a)                                                                       NO.sub.2                                                                           CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-Cl    76-82                                        3G Cl   CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-SO.sub.2 CH.sub.3                                                                   .sup. 176-179°                        4G CH.sub.3                                                                           CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-SO.sub.2 C.sub.2 H.sub.5                                                            gum                                          5G CF.sub.3                                                                           CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-CF.sub.3                                                                            viscous oil                                  6G NO.sub.2                                                                           CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-SO.sub.2 CH.sub.2 Cl                                                                oil                                          7G Cl   CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-F     gum                                          8G Cl   CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         3-OC.sub.2 H.sub.5                                                                 4-SO.sub.2 C.sub.2 H.sub.5                                                            gum                                          9G NO.sub.2                                                                           CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-SO.sub.2 CH.sub.3                                                                   gum                                         10G Cl   CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-SCH.sub.3                                                                           gum                                         11G CH.sub.3                                                                           CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         3-NO.sub.2                                                                         H       gum                                         12G I    CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    H       gum                                         13G OCH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-Cl    gum                                         14G Cl   CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         3-OCH.sub.3                                                                        4-Br    gum                                         15G NO.sub.2                                                                           CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-SO.sub.2 nC.sub.3 H.sub.7                                                           gum                                         16G NO.sub.2                                                                           CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-SO.sub.2 N(CH.sub.3).sub.2                                                          gum                                         17G NO.sub.2                                                                           CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-CN    .sup.  148-150°                      18G SO.sub.2 CH.sub.3                                                                  CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    H       gum                                         19G NO.sub.2                                                                           CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-CF.sub.3                                                                            gum                                         20G H    CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-Cl    gum                                         21G H    CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-SCF.sub.3                                                                           gum                                         22G H    CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-OCF.sub.3                                                                           gum                                         23G Cl   CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         3-Cl 4-SO.sub.2 C.sub.2 H.sub.5                                                            gum                                         24G H    CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-C(O)CH.sub.3                                                                        gum                                         25G H    CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-SO.sub.2CH.sub.3                                                                    129-131                                     26G H    CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-SCH.sub.3                                                                           89-92                                       27G H    CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-CF.sub.3                                                                            115-125                                     28G H    CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H    4-CN    87-95                                       __________________________________________________________________________     .sup.(a) prepared in Example 1G,G'.                                      

Herbicidal Screening Tests

As previously mentioned, the herein described compounds produced in theabove-described manner are phytotoxic compounds which are useful andvaluable in controlling various plant species. Selected compounds ofthis invention were tested as herbicides in the following manner.

Pre-emergence herbicide test. On the day preceding treatment, seeds ofeight different weed species are planted in loamy sand soil inindividual rows using one species per row across the width of a flat.The seeds used are green foxtail (FT) (Setaria viridis), watergrass (WG)(Echinochloa crusgalli), wild oat (WO) (Avena fatua), annualmorningglory (AMG) (Ipomoea lacunosa), velvetleaf (VL) (Abutilontheophrasti), Indian mustard (MD) (Brassica juncea), redroot pigweed(PW) (Amaranthus retroflexus) or curly dock (CD) (Rumex crispus), andyellow nutsedge (YNG) (Cyperus esculentus). Ample seeds are planted togive about 20 to 40 seedlings per row, after emergence, depending uponthe size of the plants.

Using an analytical balance, 600 milligrams (mg) of the compound to betested are weighed out on a piece of glassine weighing paper. The paperand compound are placed in a 60 milliliter (ml) wide-mouth clear bottleand dissolved in 45 ml of acetone or substituted solvent. Eighteen ml ofthis solution are transferred to a 60 ml wide-mouth clear bottle anddiluted with 22 ml of a water and acetone mixture (19:1) containingenough polyoxyethylene sorbitan monolaurate emulsifier to give a finalsolution of 0.5% (v/v). The solution is then sprayed on a seeded flat ona linear spray table calibrated to deliver 80 gallons per acre (748L/ha). The application rate is 4 lb/acre (4.48 Kg/ha).

After treatment, the flats are placed in the greenhouse at a temperatureof 70° to 80° F. and watered by sprinkling. Two weeks after treatment,the degree of injury or control is determined by comparison withuntreated check plants of the same age. The injury rating from 0 to 100%is recorded for each species as percent control with 0% representing noinjury and 100% representing complete control.

The results of the tests are shown in the following Tables

                  TABLE II-A                                                      ______________________________________                                        Pre-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                 Cmpd.                                                                         No.  FT     WG     WO   AMG   VL   MD   PW   CD   YNS                         ______________________________________                                        1A   100    90     20   40    65   50   35        80                          2A   80     90     0    30    80   90   20        90                          3A   0      0      0    40    40   40   0         0                           4A   100    100    50   35    100  100  90        95                          5A   100    95     65   35    90   85   50        95                          6A   50     25     0    25    100  100  35        80                          7A   80     90     10   60    100  100  100       80                          8A   95     95     45   40    100  80   95        95                          9A   95     100    55   30    100  90   100       95                          10A  100    100    60   20    85   100  100       95                          11A  85     100    30   40    100  100  100       95                          12A  85     85     90   75    80   95   90        90                          13A  85     75     10   10    85   65   95        90                          14A  40     10     80   0     65   40   65        100                         15A  40     60     20   30    100  30   75        95                          16A  80     80     20   55    75   90   40        95                          17A  20     --     10   25    100  95   85        90                          18A  65     --     30   70    100  100  85        90                          19A  45     60     0    30    40   0    20        60                          20A  30     85     20   40    95   85   40        45                          21A  80     100    0    80    100  100  95        95                          22A  20     10     0    20    75   30   45        10                          23A  45     95     10   0     100  85   100       95                          24A  --     100    0    25    70   90   --        100                         25A  --     100    25   80    100  100  --        100                         26A  40     15     0    0     0    10        0    30                          27A  40     80     10   20    60   50        30   75                          28A  65     75     0    65    100  95        75   55                          29A  100    95     55   10    80   75        85   95                          30A  20     20     20   10    40   40        50   20                          31A  75     95     20   20    100  95        75   10                          32A  90     85     20   0     100  85        75   30                          33A  80     70     0    40    20   40        90   80                          34A  60     40     0    20    95   100       100  60                          35A  0      10     0    0     10   20        20   10                          36A  0      0      0    20    100  100       100  0                           37A  40     0      0    20    100  60        90   --                          38A  10     40     0    20    90   80        20   20                          39A  80     10     0    0     0    0         0    90                          40A  60     0      0    0     0    0         0    90                          41A  100    100    85   40    95   100       100  100                         42A  60     100    25   0     0    0         0    25                          43A  100    100    45   40    80   90        90   100                         44A  90     100    0    60    100  100       100  95                          45A  100    100    0    60    100  100       100  100                         46A  20     60     0    100   100  100       100  20                          47A  60     70     20   100   100  100       100  60                          48A  60     0      0    0     0    0         0    40                          49A  100    100    50   10    60   20        90   100                         50A  100    100    80   10    60   60        90   100                         51A  100    100    90   100   100  100       85   100                         52A  100    100    60   10    100  100       60   100                         53A  0      20     0    0     20   20        0    10                          54A  10     45     10   0     0    0         0    40                          55A  90     100    60   100   100  100       90   100                         56A  40     70     40   40    40   60        70   50                          57A  100    100    90   100   100  100       85   100                         58A  90     95     0    20    20   40        40   100                         59A  95     100    85   75    100  100       90   98                          60A  95     100    50   50    100  100       90   98                          61A  100    100    75   100   100  100       95   95                          62A  100    100    95   75    100  100       100  80                          63A  100    100    40   65    100  100       100  95                          64A  100    100    98   100   100  100       100  90                          65A  100    100    80   100   100  100       100  90                          66A  100    100    75   100   100  100       100  98                          73A  100    100    60   80    100  100       75   90                          74A  100    100    70   80    100  100       80   100                         75A  70     100    0    50    100  100       100  80                          76A  40     90     25   10    100  100       100  10                          77A  100    100    90   100   100  100       85   --                          78A  100    100    80   100   100  100       90   --                          79A  50     100    50   50    95   100       100  60                          80A  0      0      0    0     0    0         0    0                           81A  100    100    50   15    100  100       90   100                         84A  100    100    85   0     0    100       20   100                         88A  60     95     35   95    100  100       95   80                          89A  75     100    40   100   100  100       95   60                          90A  100    100    90   100   100  100       100  85                          105A 80     95     25   0     95   50        70   50                          117A 95     100    0    25    100  100       50   95                          118A 100    100    60   100   100  100       100  85                          121A 95     100    50   75    100  95        100  80                          125A 100    100    50   80    100  100       100  55                          126A 70     100    80   80    100  100       100  80                          127A 100    100    100  100   100  100       --   80                          128A 100    100    100  100   100  100       --   80                          129A 100    100    95   90    100  100       --   80                          131A 70     85     0    20    95   98        95   90                          132A 100    100    95   90    100  100       --   80                          133A 100    100    100  100   100  100       --   80                          135A 100    100    100  80    100  100       --   80                          ______________________________________                                    

                  TABLE II-B                                                      ______________________________________                                        Pre-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                 Cmpd.                                                                         No.   FT     WG     WO   AMG   VL   MD    CD   YNS                            ______________________________________                                        1B    0      85     10   75    100  80    80   75                             2B    90     100    65   100   100  100   100  100                            4B    100    100    80   60    100  80    90   100                            5B    80     100    20   40    100  100   80   100                            6B    40     100    0    40    100  100   80   100                            7B    100    100    100  80    100  100   90   100                            8B    100    100    60   45    60   60    80   100                            9B    60     100    40   20    60   60    60   100                            10B   100    100    40   5     80   60    80   100                            11B   100    100    90   10    20   20    40   100                            12B   0      20     0    0     10   20    10   0                              13B   100    100    90   40    100  100   100  100                            15B   90     90     50   20    --   100   100  80                             16B   100    100    95   100   100  100   90   100                            17B   100    100    100  100   100  100   100  97                             18B   100    100    85   100   100  100   90   95                             19B   100    100    95   100   100  100   100  95                             20B   100    100    85   100   100  100   100  90                             21B   100    100    100  100   100  100   100  95                             22B   100    100    80   100   100  100   100  90                             25B   100    100    75   80    100  100   100  90                             26B   100    100    65   30    100  100   100  90                             27B   20     95     60   5     100  100   90   100                            28B   100    100    80   20    90   40    80   100                            29B   100    100    70   20    100  100   100  100                            30B   100    100    80   60    100  100   80   100                            31B   80     100    40   10    60   60    80   100                            32B   20     40     10   0     --   60    100  60                             33B   0      10     0    0     10   10    0    0                              34B   100    100    90   80    100  100   90   100                            35B   100    100    90   40    90   90    90   90                             36B   100    100    85   0     95   85    95   90                             37B   90     90     50   20    --   100   100  80                             39B   15     100    0    50    100  80    70   40                             40B   0      10     0    0     10   10    0    0                              41B   0      20     0    0     10   20    10   0                              42B   100    100    90   45    100  100   65   100                            43B   100    100    90   100   100  100   100  90                             44B   100    100    85   100   100  100   100  95                             45B   65     100    0    0     100  20    20   90                             46B   100    100    0    220   100  100   98   85                             47B   100    100    90   85    100  100   100  95                             48B   100    100    85   15    100  100   85   95                             49B   100    100    65   0     100  100   50   50                             50B   80     80     55   0     98   55    80   65                             51B   95     95     10   0     65   0     25   60                             52B   100    100    100  100   100  100   100  50                             53B   100    100    75   100   100  100   100  50                             54B   100    100    60   15    100  100   100  80                             55B   100    100    55   15    100  100   90   95                             56B   100    100    60   20    95   100   90   10                             57B   5      10     0    0     40   20    0    0                              58B   10     40     10   10    95   40    100  80                             59B   100    100    75   80    100  100   100  75                             60B   100    100    90   100   100  100   85   --                             61B   100    100    80   100   100  100   100  --                             62B   95     100    50   95    100  100   85   --                             63B   100    100    70   100   90   100   100  --                             64B   100    100    75   100   100  100   85   --                             65B   100    100    55   40    100  100   90   70                             66B   100    100    65   35    100  100   100  95                             67B   100    100    30   15    100  100   95   90                             71B   100    100    80   100   100  100   80   --                             72B   100    100    40   100   100  100   90   75                             73B   90     100    40   100   100  100   95   50                             74B   100    100    85   95    100  100   90   80                             75B   100    100    100  70    100  100   100  95                             77B   100    100    55   40    100  100   90   70                             81B   90     95     60   10    25   75    90   0                              82B   40     90     20   35    100  --    75   20                             91B   100    100    85   100   100  100   80   90                             101B  85     90     0    0     95   50    50   75                             ______________________________________                                    

                  TABLE II-C                                                      ______________________________________                                        Pre-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                 Cmpd.                                                                         No.   FT     WG     WO   AMG   VL   MD    CD   YNS                            ______________________________________                                        1C    65     80     65   55    90   90    35   0                              ______________________________________                                    

                  TABLE II-D                                                      ______________________________________                                        Pre-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                 Cmpd.                                                                         No.   FT     WG     WO   AMG   VL   MD    CD   YNS                            ______________________________________                                        1D    100    100    85   30    100  100   90   90                             2D    100    100    100  50    100  100   95   95                             3D    100    100    85   25    100  100   100  95                             4D    100    100    100  20    100  85    95   90                             5D    100    100    45   25    100  100   90   90                             6D    100    100    95   40    100  100   85   90                             9D    100    100    90   90    100  100   80   90                             10D   100    90     20   10    100  70    100  90                             11D   90     100    50   230   100  100   90   90                             12D   100    100    95   80    100  100   90   90                             13D   40     75     0    10    80   100   100  90                             14D   50     0      0    0     100  80    70   90                             15D   65     95     20   15    100  80    90   85                             17D   100    100    60   30    100  100   90   35                             18D   100    100    100  100   100  100   100  95                             19D   100    100    0    50    100  100   100  95                             20D   75     100    0    25    100  90    65   90                             21D   100    100    100  80    100  100   90   95                             22D   100    100    100  80    100  100   95   95                             23D   100    100    98   95    100  100   100  95                             25D   100    100    80   100   100  100   80   --                             26D   100    100    75   100   100  100   80   --                             27D   90     100    50   100   100  100   100  90                             28D   75     50     50   0     100  100   90   65                             30D   100    100    85   100   100  100   95   90                             31D   85     75     0    25    100  25    0    35                             32D   83     85     35   20    95   100   75   50                             36D   100    100    50   100   100  100   100  75                             37D   20     75     0    20    100  95    100  75                             38D   85     95     40   60    100  100   75   85                             39D   85     95     45   75    100  95    70   90                             51D   60     60     35   0     25   0     0    30                             52D   75     75     0    50    90   75    40   0                              65D   100    100    80   100   100  100   --   80                             ______________________________________                                         A blank (--) indicates that the weed was not tested.                     

                  TABLE II-E                                                      ______________________________________                                        Pre-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                 Cmpd.                                                                         No.   FT     WG     WO   AMG   VL   MD    CD   YNS                            ______________________________________                                        1E    0      0      0    0     0    0     0    20                             2E    25     30     30   0     70   0     40   30                             3E    25     20     0    0     0    0     0    0                              4E    100    100    90   60    100  100   100  90                             5E    50     60     40   50    50   60    90   50                             6E    100    95     50   40    40   60    99   70                             16E   80     100    50   60    100  90    90   90                             20E   100    100    30   15    100  100   90   85                             21E   100    100    --   30    100  95    100  80                             ______________________________________                                         A blank (--) indicates that the weed was not tested.                     

                  TABLE II-F                                                      ______________________________________                                        Pre-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                 Cmpd.                                                                         No.   FT     WG     WO   AMG   VL   MD    CD   YNS                            ______________________________________                                        1F    40     20     0    0     0    0     0    100                            2F    60     70     0    0     0    0     90   100                            3F    100    100    50   50    100  100   85   90                             4F    100    100    90   30    100  85    95   95                             5F    100    100    80   10    100  100   100  95                             6F    20     35     25   15    90   85    40   85                             7F    100    100    90   100   100  100   100  95                             8F    100    100    90   100   100  100   100  95                             9F    100    100    0    0     100  80    100  90                             10F   100    100    100  100   100  100   100  95                             11F   100    100    70   100   100  100   97   95                             12F   100    100    60   100   100  100   100  95                             13F   100    100    60   100   100  100   100  95                             14F   80     100    50   80    100  100   90   90                             15F   100    100    80   100   100  100   100  --                             16F   50     75     0    25    100  100   95   60                             17F   100    100    40   100   100  100   100  85                             18F   100    100    0    20    100  100   80   70                             20F   70     75     0    25    100  95    100  60                             21F   50     60     0    0     100  80    80   60                             22F   100    95     35   25    100  100   90   50                             23F   95     100    40   20    100  100   90   50                             24F   100    100    90   0     45   85    80   90                             25F   100    100    25   60    100  100   100  75                             34F   35     40     10   0     60   25    0    70                             37F   50     60     0    0     60   0     50   0                              38F   35     40     0    0     0    0     0    0                              52F   85     100    30   95    100  100   --   80                             53F   100    100    0    85    100  100   --   80                             54F   100    100    90   25    100  100   --   80                             ______________________________________                                         A blank (--) indicates that the weed was not tested.                     

                  TABLE II-G                                                      ______________________________________                                        Pre-Emergence Herbicidal Activity                                             Application Rate - 4.48 kg/ha                                                 Cmpd.                                                                         No.   FT     WG      WO    AMG   VL    MD    YNS                              ______________________________________                                        1G    100    100     90    100   100   100   80                               2G    100    100     90    100   100   100   80                               3G    100    100     90    100   100   100   80                               4G    100    100     90    100   100   100   80                               5G    100    100     90    100   100   100   80                               6G*   100    100     100   100   100   --    20                               7G    100    100     80    100   100   100   80                               8G    85     100     80    100   100   100   80                               9G    100    100     80    100   100   100   80                               10G   100    100     80    100   100   100   80                               11G   100    100     80    100   100   100   80                               12G   100    100     80    90    100   100   0                                13G   100    100     70    100   100   100   0                                14G   100    100     75    100   100   100   90                               15G   100    100     80    100   100   100   90                               16G   100    100     90    100   100   100   80                               17G   100    100     80    100   100   100   80                               18G   100    100     90    85    100   100   80                               19G   100    100     100   100   100   100   80                               20G   70     95      10    100   100   100   0                                21G   100    100     100   100   100   100   80                               22G   100    100     90    100   100   100   80                               23G   100    100     100   100   100   100   80                               24G   0      80      0     25    80    70    0                                25G   100    100     80    100   100   100   80                               26G   100    100     100   80    100   100   80                               27G   100    100     100   100   100   100   80                               28G   100    100     90    100   100   100   80                               ______________________________________                                         A blank (--) indicates that the weed was not tested.                           *Tested at 0.56 kg/ha.                                                  

Post-Emergence Herbicide Test: This test is conducted in an identicalmanner to the testing procedure for the pre-emergence herbicide test,except the seeds of the eight different weed species are planted 10-12days before treatment. Also, watering of the treated flats is confinedto the soil surface and not to the foliage of the sprouted plants.

The results of the post-emergence herbicide test are reported in TableIII.

                  TABLE III-A                                                     ______________________________________                                        Post-Emergence Herbicidal Activity                                            Application Rate - 4.48 kg/ha                                                 Cmpd.                                                                         No.   FT     WG     WO   AMG   VL   MD   PW CD  YNS                           ______________________________________                                        1A    60     70     20   40    60   60   35     60                            2A    30     70     0    50    90   85   30     80                            3A    0      30     0    70    100  90   55     70                            4A    95     98     20   98    100  100  30     95                            5A    80     80     75   50    60   80   0      95                            6A    40     40     10   60    100  100  75     65                            7A    60     75     40   60    100  75   100    75                            8A    85     80     75   70    95   80   90     90                            9A    85     80     75   70    95   80   90     90                            10A   95     85     90   60    95   95   80     95                            11A   50     80     35   55    100  100  95     80                            12A   45     75     50   55    75   60   50     80                            13A   30     60     20   60    80   50   60     70                            14A   20     10     20   50    45   40   40     0                             15A   65     95     0    65    95   30   100    80                            16A   65     80     20   85    85   30   30     80                            17A   75     80     30   70    100  100  85     90                            18A   100    95     10   100   100  100  100    90                            19A   60     80     40   70    100  75   80     90                            20A   65     80     10   85    95   95   100    70                            21A   30     55     0    80    100  80   65     80                            22A   0      30     0    20    45   0    30     20                            23A   85     90     40   85    100  95   100    90                            24A   0      80     0    70    90   74   --     100                           25A   100    100    75   90    100  100  --     100                           26A   45     30     0    40    70   65   0      45                            27A   75     80     30   65    50   45   85     85                            28A   75     60     60   75    100  70   80     25                            29A   85     85     85   75    85   65   65     85                            30A   75     50     20   10    0    0    20     40                            31A   60     60     20   40    40   70   100    40                            32A   60     25     20   40    90   65   20     40                            33A   10     0      0    10    10   10   100    40                            34A   10     10     0    5     50   30   80     0                             35A   0      0      0    10    60   30   40     0                             36A   0      0      0    20    20   20   0      0                             37A   0      0      0    30    40   20   80     0                             38A   10     10     10   20    10   20   20     10                            39A   40     40     20   0     0    0    5      80                            40A   90     70     40   20    60   80   20     65                            41A   60     85     85   20    40   60   100    100                           42A   60     50     40   70    20   40   60     60                            43A   100    80     30   60    100  100  80     100                           44A   80     85     0    60    90   90   100    80                            45A   90     90     10   100   100  100  100    90                            46A   80     100    0    60    100  100  100    100                           47A   100    100    0    60    100  100  100    100                           48A   40     40     20   10    10   10   90     40                            49A   40     40     40   80    100  100  60     60                            50A   80     60     60   50    50   60   80     70                            51A   80     80     80   95    100  100  100    90                            52A   60     60     20   20    40   40   90     60                            53A   10     20     20   0     0    0    0      20                            54A   20     40     20   5     0    0    0      40                            55A   40     40     40   60    60   60   80     90                            56A   100    100    75   80    100  100  100    90                            57A   80     80     80   95    100  100  100    90                            58A   60     70     10   70    10   10   20     80                            59A   100    100    90   100   --   100  100    50                            60A   100    100    100  100   --   100  100    70                            61A   90     85     90   85    --   100  100    80                            62A   100    85     100  75    100  100  100    35                            63A   70     80     20   100   100  100  35     40                            64A   75     75     90   70    90   70   40     40                            65A   100    70     100  55    90   95   100    40                            66A   100    75     100  90    95   95   100    20                            73A   100    100    95   100   100  100  55     30                            74A   100    95     75   100   100  100  85     40                            75A   100    100    30   95    80   100  80     40                            76A   80     80     75   75    100  95   95     25                            77A   80     80     80   90    90   80   90     80                            78A   80     85     75   85    80   95   100    50                            79A   50     65     35   90    100  100  90     --                            80A   40     40     10   20    60   0    0      30                            81A   90     70     60   40    60   60   90     70                            84A   100    100    100  20    40   40   80     60                            88A   100    95     90   100   85   100  100    50                            89A   100    100    75   85    75   85   95     50                            90A   100    85     90   90    85   90   100    55                            91A   100    100    100  100   95   100  95     60                            105A  35     50     --   35    100  80   60     30                            117A  40     60     0    25    50   50   80     --                            118A  95     85     85   100   100  90   80     80                            121A  65     85     40   100   100  100  60     50                            125A  90     95     75   70    100  90   100    60                            126A  40     50     20   40    60   50   100    80                            127A  100    95     100  95    100  100         80                            128A  85     95     80   60    100  95          80                            129A  65     90     60   60    100  98          70                            130A  100    95     95   95    100  100         70                            131A  0      20     0    0     30   75   10     0                             132A  95     100    100  80    95   95          50                            133A  80     95     90   60    85   85          60                            135A  70     100    100  75    100  95          70                            ______________________________________                                    

                  TABLE III-B                                                     ______________________________________                                        Post-Emergence Herbicidal Activity                                            Application Rate - 4.48 kg/ha                                                 Cmpd.                                                                         No.   FT     WG      WO   AMG   VL   MD    CD   YNS                           ______________________________________                                         1B   85     95      20   95    100  100   95   95                             2B   90     90      80   100   90   90    --   80                             4B   60     60      90   40    60   60    90   70                             5B   40     60      10   20    40   40    90   80                             6B   40     50      10   60    20   20    60   50                             7B   80     80      80   60    60   90    6    60                             8B   100    80      60   30    80   80    80   80                             9B   70     70      60   40    60   60    80   70                            10B   40     40      60   30    60   60    90   60                            11B   80     90      60   45    90   90    100  80                            12B   25     45      10   20    20   20    60   45                            13B   100    100     95   70    60   60    80   60                            15B   100    60      50   80    90   90    40   60                            16B   60     60      80   80    90   90    60   65                            17B   100    70      90   100   --   90    98   70                            18B   100    85      100  85    --   100   100  65                            19B   100    80      85   100   100  90    100  70                            20B   90     65      90   85    70   60    100  40                            21B   40     40      10   0     0    0     0    0                             22B   40     70      80   90    90   100   95   40                            25B   40     70      40   40    40   60    70   50                            26B   65     70      80   40    90   80    70   80                            27B   100    80      60   20    90   90    80   45                            28B   90     60      60   60    60   60    40   70                            29B   90     70      70   40    70   70    60   60                            30B   100    90      70   50    100  100   80   80                            31B   40     50      20   10    20   20    0    40                            32B   25     40      40   90    100  100   40   40                            33B   20     40      10   60    90   90    60   40                            34B   90     80      80   80    100  100   80   50                            35B   60     50      50   20    60   60    80   60                            36B   100    80      80   75    --   100   100  45                            37B   100    60      50   80    90   90    40   60                            39B   90     80      25   30    30   45    50   30                            40B   20     40      10   60    90   90    60   40                            41B   25     45      10   20    20   20    60   45                            42B   90     80      80   80    100  100   100  70                            43B   80     90      95   97    100  100   100  50                            44B   100    95      95   95    40   100   100  30                            45B   30     65      0    30    45   40    65   50                            46B   70     75      0    65    100  100   50   70                            47B   100    100     100  90    100  100   100  85                            48B   100    65      80   50    100  100   60   60                            49B   60     70      70   40    80   70    30   50                            50B   0      60      40   60    100  90    20   30                            51B   100    75      80   40    100  50    20   30                            52B   90     100     100  100   100  100   100  40                            53B   60     70      70   70    90   65    40   60                            54B   100    100     85   100   100  100   100  60                            55B   95     85      90   100   100  100   90   45                            56B   85     100     0    10    15   95    40   50                            57B   85     70      65   0     0    0     0    35                            58B   20     40      10   15    70   40    35   40                            59B   100    95      100  95    100  95    100  40                            60B   65     75      75   80    90   85    80   60                            61B   80     80      70   95    80   85    80   50                            62B   100    80      25   80    75   80    85   35                            63B   100    100     40   95    95   100   95   50                            64B   75     70      50   90    90   100   90   50                            65B   100    80      80   60    85   60    0    --                            66B   98     90      60   35    --   100   60   90                            67B   70     65      20   15    95   40    70   45                            71B   95     50      50   80    80   80    65   50                            72B   100    85      75   75    65   85    70   60                            73B   100    95      95   85    75   85    95   40                            74B   100    85      95   90    80   95    65   50                            75B   100    80      80   30    50   60    100  40                            81B   50     80      35   70    70   90    80   10                            82B   25     60      50   35    50   90    50   25                            91B   80     60      40   60    75   90    60   75                            101B  10     35      --   30    75   70    40   50                            ______________________________________                                         (--) = Specie did not germinate for some reason.                         

                  TABLE III-C                                                     ______________________________________                                        Post-Emergence Herbicidal Activity                                            Application Rate - 4.48 kg/ha                                                 Cmpd.                                                                         No.   FT     WG      WO   AMG   VL   MD    CD   YNS                           ______________________________________                                        1C    98     95      70   60    100  55    100  90                            ______________________________________                                    

                  TABLE III-D                                                     ______________________________________                                        Post-Emergence Herbicidal Activity                                            Application Rate - 4.48 kg/ha                                                 Cmpd.                                                                         No.   FT     WG     WO   AMG   VL   MD    CD   YNS                            ______________________________________                                        1D    95     75     85   70    100  90    85   40                             2D    45     70     95   75    100  90    100  65                             3D    100    80     100  90    --   100   100  80                             4D    100    80     100  100   --   100   85   75                             5D    90     70     45   60    95   70    60   80                             6D    95     75     80   70    100  90    90   65                             9D    100    90     90   100   100  100   95   85                             10D   45     75     10   15    100  100   20   75                             11D   100    70     60   75    100  100   100  45                             12D   100    75     100  100   100  100   90   90                             13D   30     55     0    30    60   60    15   60                             14D   20     65     0    40    70   60    40   25                             15D   20     75     30   20    100  70    60   40                             17D   85     80     50   65    95   95    100  60                             18D   100    95     100  100   100  100   100  75                             19D   20     95     30   100   100  35    30   70                             20D   30     80     15   100   100  45    20   70                             21D   100    80     100  55    100  90    100  80                             22D   100    80     100  60    100  95    95   95                             23D   100    90     90   100   100  100   85   70                             25D   70     75     50   85    90   85    60   75                             26D   100    85     85   95    95   95    90   60                             27D   90     90     60   100   100  100   100  --                             28D   15     45     20   50    75   80    15   30                             30D   100    100    80   85    85   85    100  --                             31D   80     90     100  100   100  100   100  60                             32D   75     85     85   75    75   90    95   50                             36D   35     50     35   70    50   50    35   60                             37D   60     75     15   70    70   90    90   40                             38D   95     90     65   70    90   90    100  50                             39D   95     85     30   50    70   80    100  50                             51D   60     75     60   35    30   60    40   60                             52D   60     75     25   100   100  100   100  75                             65D   70     50     70   90    80   85    --   80                             ______________________________________                                         A blank (--) indicates the weed was not tested.                          

                  TABLE III-E                                                     ______________________________________                                        Post-Emergence Herbicidal Activity                                            Application Rate - 4.48 kg/ha                                                 Cmpd.                                                                         No.   FT     WG     WO   AMG   VL   MD    CD   YNG                            ______________________________________                                        1E    20     20     10   20    40   40    20   40                             2E    0      60     60   50    70   30    0    15                             3E    20     20     0    10    0    20    0    20                             4E    85     90     100  45    75   30    80   65                             5E    55     50     60   50    75   85    65   --                             6E    70     70     50   60    80   70    90   --                             16E   95     95     40   100   100  100   100  90                             20E   95     75     35   40    95   75    35   80                             21E   80     70     30   45    80   90    50   70                             ______________________________________                                         A blank (--) indicates the weed was not tested.                          

                  TABLE III-F                                                     ______________________________________                                        Post-Emergence Herbicidal Activity                                            App1ication Rate - 4.48 kg/ha                                                 Cmpd.                                                                         No.   FT     WG     WO   AMG   VL   MD    CD   YNG                            ______________________________________                                        1F    60     40     20   30    40   40    50   60                             2F    50     40     10   20    20   20    40   60                             3F    100    100    85   100   100  100   100  75                             4F    100    100    95   85    100  95    100  60                             5F    95     95     100  65    90   25    70   45                             6F    40     30     0    20    90   25    20   70                             7F    100    100    100  100   100  100   100  90                             8F    100    95     100  100   100  100   100  70                             9F    65     65     0    20    80   65    90   80                             10F   100    100    100  100   100  100   100  70                             11F   85     90     90   85    90   80    30   60                             12F   100    90     65   80    100  100   100  50                             13F   100    95     100  100   100  100   90   --                             14F   100    100    100  100   100  100   100  50                             15F   25     35     15   30    80   25    20   0                              16F   100    85     70   75    90   90    50   --                             17F   100    100    100  100   100  100   100  --                             18F   90     85     85   85    90   95    70   40                             20F   40     60     10   60    100  100   100  50                             21F   35     60     10   60    100  100   80   60                             22F   95     95     35   100   100  100   90   50                             23F   100    100    40   100   100  100   90   50                             24F   100    75     100  60    --   100   100  60                             25F   95     95     90   95    100  100   95   35                             34F   50     40     0    35    50   70    30   50                             37F   20     60     0    30    30   50    50   50                             38F   25     50     0    25    25   50    20   20                             52F   0      60     50   50    10   50    --   20                             53F   0      50     0    50    50   50    --   30                             54F   90     75     60   50    50   80    --   80                             ______________________________________                                         A blank (--) indicates the weed was not tested.                          

                  TABLE III-G                                                     ______________________________________                                        Post-Emergence Herbicidal Activity                                            Application Rate - 4.48 kg/ha                                                 Cmpd.                                                                         No.   FT      WG      WO   AMG   VL    MD    YNG                              ______________________________________                                         1G   100     95      90   90    100   100   80                                2G   100     100     100  100   100   100   80                                3G   100     100     95   100   100   100   90                                4G   100     100     100  100   100   100   90                                5G   100     100     100  100   100   100   100                               6G*  10      80      50   75    40    --    0                                 7G   70      75      70   90    90    80    80                                8G   50      80      70   90    90    80    30                                9G   70      80      70   90    90    80    30                               10G   75      80      70   80    60    50    70                               11G   70      80      70   80    80    80    80                               12G   100     75      90   75    80    80    80                               13G   60      70      70   100   100   100   80                               14G   20      70      40   60    80    80    70                               15G   90      70      70   75    80    90    70                               16G   50      70      80   60    80    90    70                               17G   90      60      70   65    80    80    80                               18G   30      50      80   95    95    80    70                               19G   100     100     95   90    100   100   80                               20G   10      40      5    70    80    90    70                               21G   95      90      95   95    100   100   70                               22G   80      90      90   80    100   100   70                               23G   90      80      80   80    90    80    30                               24G   0       30      0    40    80    20    0                                25G   0       20      0    10    10    20    0                                26G   80      70      70   80    80    80    70                               27G   90      90      90   80    80    90    60                               28G   70      65      50   80    80    80    70                               ______________________________________                                         A blank (--) indicates the weed was not tested.                               * = Tested at 0.56 kg/ha.                                                

Pre-Emergence Multi-Weed Herbicide Test

Several compounds were evaluated at an application rate of 2 lb/acre(2.24 kg/ha) or 1 lb/acre (1.12 kg/ha) for pre-emergence activityagainst a larger number of weed species.

The process was generally similar to the pre-emergence herbicide testdescribed above except that only 300 or 150 milligrams of test compoundwere weighed out and the application rate was 40 gallons per acre.

Redroot pigweed (PW) and curly dock (CD) were eliminated in this testand the following weed species were added:

    ______________________________________                                        Grasses:                                                                             downy brome   Bromus tectorum                                                                             (DB)                                              annual ryegrass                                                                             Lolium multiflorum                                                                          (ARG)                                             rox-orange sorghum                                                                          Sorghum bicolor                                                                             (SHC)                                             hemp sesbania Sesbania exaltata                                                                           (SESB)                                            nightshade    Solanum sp.   (SP)                                              cocklebur     Xattiium sp.  (CB)                                       ______________________________________                                    

The results of the 2.24 kg/ha test are shown in Table IV and the resultsof the 1.12 kg/ha test are shown in Table VI.

Post-Emergence Multi-Weed Herbicide Test

Several compounds were evaluated at an application rate of 2 lb/acre(2.24 kg/ha) or 1 lb/acre (1.12 kg/ha) for post-emergence activityagainst the larger number of weed species that are used in thepre-emergent multi-herbicide test.

The process was generally similar to the post-emergence herbicide testdescribed above except that only 300 or 150 milligrams of test compoundwere weighed out and the application rate was 40 gallons per acre.

The results of the 2.24 kg/ha test are shown in Table V and the resultsfor the 1.12 kg/ha test are shown in Table VII.

                                      TABLE IV-A                                  __________________________________________________________________________    Pre-Emergence Multi-weed Herbicide Test                                       Application Rate - 2.24 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG SHC                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                              __________________________________________________________________________    67A 20 90 25  98 80 60 90 45  90  45 20 85 85 15                              68A 65 98 98  100                                                                              100                                                                              60 95 100 100 100                                                                              80 100                                                                              95 100                             69A 65 100                                                                              70  100                                                                              100                                                                              65 95 100 95  70 65 100                                                                              90 --                              70A 98 100                                                                              100 100                                                                              100                                                                              90 98 90  100 90 60 100                                                                              95 80                              71A 60 20 100 100                                                                              100                                                                              80 95 35  40  100                                                                              20 90 100                                                                              40                              72A 100                                                                              100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              100 90  100                                                                              60 100                                                                              100                                                                              20                              83A 15 45 25  90 15 5  90 45  35  20 0  20 75 --                              86A 20 0  15  60 60 20 70 25  45  100                                                                              20 100                                                                              15 35                              87A 100                                                                              90 85  100                                                                              85 25 30 35  85  100                                                                              85 100                                                                              95 40                              __________________________________________________________________________

                                      TABLE VI-A                                  __________________________________________________________________________    Post-Emergence Multi-weed Herbicide Test                                      Application Rate - 2.24 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG SHC                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                              __________________________________________________________________________    86A 60 100                                                                              50  90 50 60 90 70  100 100                                                                              20 100                                                                              20 --                              87A 95 100                                                                              30  100                                                                              80 70 80 95  100 100                                                                              100                                                                              100                                                                              70 --                              __________________________________________________________________________

                                      TABLE V-A                                   __________________________________________________________________________    Pre-Emergence Multi-weed Herbicide Test                                       Application Rate - 1.12 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG SHC                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                              __________________________________________________________________________     82A                                                                              35 100                                                                              85  100                                                                              65 60 90 50  90  60 30 97 90 40                               85A                                                                              100                                                                              100                                                                              100 100                                                                              100                                                                              85 100                                                                              20  10  100                                                                              65 100                                                                              100                                                                              30                               92A                                                                              15 20 45  100                                                                              90 40 80 95  95  100                                                                              25 100                                                                              90 40                               93A                                                                              30 75 40  100                                                                              100                                                                              60 90 100 100 100                                                                              35 100                                                                              90 40                               94A                                                                              30 70 40  100                                                                              100                                                                              30 65 95  85  100                                                                              0  100                                                                              90 30                               95A                                                                              0  0  0   85 60 15 70 65  60  100                                                                              80 90 10 20                               96A                                                                              95 100                                                                              98  100                                                                              100                                                                              70 100                                                                              100 95  90 80 100                                                                              95 --                               97A                                                                              100                                                                              100                                                                              98  100                                                                              100                                                                              100                                                                              100                                                                              100 95  100                                                                              70 100                                                                              95 100                              98A                                                                              10 0  0   0  20 25 70 0   20  0  0  80 30 --                               99A                                                                              15 0  0   75 25 0  20 30  60  15 20 30 25 0                               100A                                                                              0  0  0   0  0  0  20 10  0   0  0  15 0  --                              101A                                                                              100                                                                              98 95  100                                                                              100                                                                              70 98 100 100 100                                                                              20 100                                                                              95 --                              102A                                                                              25 20 35  100                                                                              100                                                                              45 95 70  100 100                                                                              60 100                                                                              90 --                              103A                                                                              80 60 45  100                                                                              100                                                                              40 90 65  90  100                                                                              0  100                                                                              95 0                               106A                                                                              100                                                                              100                                                                              60  40 95 35 100                                                                              35  90  100                                                                              70 100                                                                              90 --                              107A                                                                              100                                                                              100                                                                              100 100                                                                              100                                                                              90 100                                                                              100 100 100                                                                              80 100                                                                              95 30                              108A                                                                              100                                                                              100                                                                              100 100                                                                              100                                                                              85 100                                                                              100 100 100                                                                              30 100                                                                              95 100                             .sup. 109A.sup.a                                                                  65 20 85  100                                                                              98 60 90 30  50  100                                                                              50 100                                                                              90 100                             110A                                                                              0  60 30  100                                                                              65 25 65 25  30  100                                                                              0  100                                                                              60 0                               111A                                                                              100                                                                              100                                                                              100 100                                                                              100                                                                              75 98 100 100 100                                                                              90 100                                                                              -- 70                              112A                                                                              100                                                                              100                                                                              90  100                                                                              100                                                                              95 100                                                                              100 100 100                                                                              100                                                                              100                                                                              -- --                              113A                                                                              65 95 40  100                                                                              100                                                                              30 90 70  100 100                                                                              0  100                                                                              -- 30                              114A                                                                              70 100                                                                              25  100                                                                              100                                                                              40 100                                                                              100 100 100                                                                              30 100                                                                              95 80                              115A                                                                              100                                                                              100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              45 100                                                                              85 100                             116A                                                                              25 15 20  100                                                                              65 35 65 45  50  100                                                                              0  100                                                                              95 10                              119A                                                                              100                                                                              100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              95 100                                                                              95 90                              120A                                                                              100                                                                              100                                                                              100 100                                                                              100                                                                              95 100                                                                              100 100 100                                                                              100                                                                              100                                                                              90 100                             122A                                                                              80 80 45  100                                                                              60 65 70 100 100 100                                                                              100                                                                              100                                                                              90 100                             123A                                                                              0  100                                                                              50  100                                                                              85 0  60 100 90  100                                                                              80 100                                                                              100                                                                              20                              124A                                                                              25 50 65  90 65 0  40 75  80  100                                                                              40 90 80 60                              __________________________________________________________________________     .sup.a application rate was 0.56 kg/ha.                                  

                                      TABLE VII-A                                 __________________________________________________________________________    Post-Emergence Multi-weed Herbicide Test                                      Application Rate - 1.12 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG SHC                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                              __________________________________________________________________________     82A                                                                              60 40 10  98 35 10 30 70  100 100                                                                              100                                                                              90 45 --                               85A                                                                              60 60 35  100                                                                              45 60 85 50  100 100                                                                              100                                                                              100                                                                              60 --                               92A                                                                              70 55 20  80 80 45 100                                                                              95  90  80 20 95 70 90                               93A                                                                              90 90 70  95 95 75 90 98  95  85 35 100                                                                              60 90                               94A                                                                              100                                                                              85 45  90 100                                                                              90 100                                                                              100 90  90 30 100                                                                              60 85                               95A                                                                              20 60 0   80 70 0  45 60  75  90 0  65 20 --                               96A                                                                              95 100                                                                              90  95 100                                                                              80 95 100 100 100                                                                              70 100                                                                              70 90                               97A                                                                              100                                                                              100                                                                              95  100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              90 100                                                                              70 100                              98A                                                                              20 0  0   45 10 50 30 20  65  100                                                                              0  75 35 80                               99A                                                                              25 75 15  80 65 10 25 85  100 100                                                                              80 100                                                                              10 --                              100A                                                                              10 35 0   70 50 5  20 30  70  40 0  100                                                                              10 100                             101A                                                                              30 60 25  100                                                                              60 60 80 100 100 100                                                                              30 100                                                                              70 --                              103A                                                                              90 100                                                                              25  100                                                                              100                                                                              80 100                                                                              100 100 100                                                                              15 100                                                                              40 --                              104A                                                                              98 98 25  98 100                                                                              15 100                                                                              100 100 100                                                                              60 100                                                                              95 --                              106A                                                                              75 90 30  90 70 25 100                                                                              100 100 100                                                                              80 100                                                                              75 --                              107A                                                                              100                                                                              100                                                                              80  90 85 100                                                                              100                                                                              100 100 100                                                                              60 100                                                                              40 --                              108A                                                                              100                                                                              100                                                                              65  90 60 95 100                                                                              100 100 100                                                                              90 100                                                                              90 --                              .sup. 109A.sup.a                                                                  90 60 45  90 70 60 98 95  95  100                                                                              98 80 55 --                              110A                                                                              50 50 20  100                                                                              50 10 40 100 98  98 20 100                                                                              35 45                              111A                                                                              85 90 80  90 70 60 95 100 90  100                                                                              65 100                                                                              80 60                              112A                                                                              100                                                                              100                                                                              90  100                                                                              100                                                                              95 100                                                                              100 100 100                                                                              45 100                                                                              95 70                              113A                                                                              70 50 20  90 60 50 80 95  95  100                                                                              60 100                                                                              -- 60                              114A                                                                              85 100                                                                              15  100                                                                              100                                                                              60 00 100 100 100                                                                              100                                                                              100                                                                              60 --                              115A                                                                              100                                                                              100                                                                              45  100                                                                              100                                                                              80 100                                                                              100 100 100                                                                              100                                                                              100                                                                              90 --                              116A                                                                              80 60 25  90 35 40 45 75  90  100                                                                              40 90 75 60                              119A                                                                              60 70 30  95 70 20 90 100 100 100                                                                              90 100                                                                              30 85                              120A                                                                              75 90 60  95 80 45 100                                                                              100 90  100                                                                              65 100                                                                              35 100                             122A                                                                              60 90 15  100                                                                              30 15 15 100 100 100                                                                              75 100                                                                              45 95                              123A                                                                              0  100                                                                              35  100                                                                              50 15 85 100 100 100                                                                              100                                                                              100                                                                              70 85                              124A                                                                              25 100                                                                              35  40 35 0  40 95  100 100                                                                              100                                                                              100                                                                              85 75                              __________________________________________________________________________     .sup.a Application rate was 0.56 kg/ha.                                       A dash mark (--) is used in Tables II-VII to indicate that no percent         control number was available.                                            

                                      TABLE IV-B                                  __________________________________________________________________________    Pre-Emergence Multi-Weed Herbicide Test                                       Application Rate - 2.24 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG SHC                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                              __________________________________________________________________________    14B 80 100                                                                              100 100                                                                              100                                                                              80 95 70  60  100                                                                              40 85 100                                                                              10                              21B 85 100                                                                              90  100                                                                              100                                                                              85 100                                                                              100 100 100                                                                              70 100                                                                              95 100                             24B 100                                                                              100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              75 100                                                                              95 --                              38B 100                                                                              100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              20  10  100                                                                              20 95 100                                                                              20                              88B 75 100                                                                              60  100                                                                              100                                                                              70 60 20  40  100                                                                              0  100                                                                              60 20                              89B 20 60 30  85 95 55 40 15  20  65 0  100                                                                              35 50                              90B 60 100                                                                              60  100                                                                              100                                                                              45 30 100 100 100                                                                              15 100                                                                              50 85                              103B                                                                              95 100                                                                              75  100                                                                              100                                                                              50 85 100 100 100                                                                              80 100                                                                              80 40                              104B                                                                              60 100                                                                              60  100                                                                              100                                                                              45 30 100 100 100                                                                              15 100                                                                              50 85                              __________________________________________________________________________     (--) = Specie did not germinate for some reason.                         

                                      TABLE V-B                                   __________________________________________________________________________    Post-Emergence Multi-Weed Herbicide Test                                      Application Rate - 2.24 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG SHC                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                              __________________________________________________________________________    24B 35 25 45  60 65 85 90 100 100 -- 90 100                                                                              65 --                              88B 60 30 30  90 100                                                                              80 100                                                                              100 100 100                                                                              30 100                                                                              20 100                             89B 50 70 35  90 60 35 20 100 90  100                                                                              35 100                                                                              15 100                             90B 30 100                                                                              40  100                                                                              70 10 25 100 100 100                                                                              30 90 50 95                              103B                                                                              95 100                                                                              70  100                                                                              65 75 65 100 100 100                                                                              65 100                                                                              50 100                             104B                                                                              30 100                                                                              40  100                                                                              70 10 25 100 100 100                                                                              30 90 50 95                              __________________________________________________________________________     (--) = Specie did not germinate for some reason.                         

                                      TABLE VI-B                                  __________________________________________________________________________    Pre-Emergence Multi-Weed Herbicide Test                                       Application Rate - 1.12 kg/ha                                                 Cmpd.                                                                         No.  DB FT ARG WG SHC                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                             __________________________________________________________________________     1B  25 10 30  85 55 0  -- 55  --  100                                                                              -- 75 75 35                             23B  55 95 90  100                                                                              95*                                                                              95 95 98  80  -- 10 100                                                                              95 --                             68B  65 100                                                                              60  100                                                                              100*                                                                             6  90 100 90  100                                                                              20 100                                                                              30 40                             69B  70 100                                                                              60  100                                                                              100*                                                                             95 95 100 95  100                                                                              0  100                                                                              85 25                             70B  60 100                                                                              75  100                                                                              100*                                                                             85 100                                                                              100 90  100                                                                              25 100                                                                              90 25                             76B  100                                                                              100                                                                              85  100                                                                              100*                                                                             85 98 100 95  -- 35 100                                                                              95 --                             78B  40 70 15  95 75*                                                                              25 80 65  75  -- 0  100                                                                              80 --                             79B  100                                                                              100                                                                              100 100                                                                              100                                                                              98 100                                                                              100 85  100                                                                              85 100                                                                              95 --                             80B  98 100                                                                              95  100                                                                              100                                                                              60 98 99  90  100                                                                              35 100                                                                              85 --                             83B  20 100                                                                              60  100                                                                              100*                                                                             40 90 85  65  100                                                                              0  100                                                                              85 --                             84B  0  90 25  98 100*                                                                             30 90 20  35  100                                                                              5  100                                                                              50 --                             85B  80 100                                                                              50  100                                                                              100                                                                              60 90 100 90  100                                                                              0  100                                                                              95 --                             86B  60 90 40  100                                                                              100                                                                              60 70 35  60  100                                                                              100                                                                              100                                                                              -- --                             87B  0  90 15  100                                                                              85 15 70 40  60  100                                                                              40 90 20 --                             92B  20 40 10  95 40 10 60 65  30  100                                                                              0  55 60 0                              93B  60 95 20  100                                                                              100                                                                              75 100                                                                              100 100 100                                                                              0  100                                                                              40 35                             94B  0  80 40  100                                                                              95 25 85 80  40  100                                                                              10 85 55 10                             95B  98 100                                                                              30  100                                                                              100                                                                              40 90 100 100 100                                                                              40 100                                                                              90 30                             96B  100                                                                              100                                                                              75  100                                                                              100                                                                              95 100                                                                              100 100 100                                                                              60 100                                                                              85 100                            97B  100                                                                              100                                                                              90  100                                                                              100                                                                              95 100                                                                              100 100 100                                                                              60 100                                                                              95 100                            98B  95 100                                                                              100 100                                                                              100                                                                              80 100                                                                              100 100 100                                                                              50 100                                                                              100                                                                              60                              99B**                                                                             -- 100                                                                              75  100                                                                              100*                                                                             20 75 50  75  95 0  -- 85 30                             100B 100                                                                              98 98  100                                                                              100                                                                              90 95 100 75  100                                                                              70 100                                                                              95 40                             102B 0  100                                                                              25  100                                                                              90 75 95 60  60  100                                                                              30 100                                                                              90 --                             __________________________________________________________________________     *seedling johnsongrass (Sorghum halepense) was substituted for roxorange      sorghum.                                                                      **Application rate was 0.56 kg/ha                                             (--) = Specie dd not germinate for some reason.                          

                                      TABLE VII-B                                 __________________________________________________________________________    Post-Emergence Multi-Weed Herbicide Test                                      Application Rate - 1.12 kg/ha                                                 Cmpd.                                                                         No.  DB FT ARG WG SHC                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                             __________________________________________________________________________     1B  45 35 40  90 35 10 -- 60  --  75 -- 60 50 55                             23B  90 100                                                                              80  90 90*                                                                              90 90 80  90  90 40 70 25 --                             68B  50 60 40  85 80*                                                                              75 100                                                                              95  90  85 55 100                                                                              40 --                             69B  70 80 35  90 90*                                                                              80 90 80  85  90 20 90 25 --                             70B  100                                                                              90 80  100                                                                              100*                                                                             95 100                                                                              100 95  80 30 75 45 90                             76B  100                                                                              100                                                                              98  100                                                                              100*                                                                             100                                                                              100                                                                              100 100 100                                                                              60 100                                                                              40 --                             78B  100                                                                              90 80  85 100*                                                                             70 90 100 100 100                                                                              0  90 45 --                             79B  80 35 45  70 60*                                                                              70 70 45  98  100                                                                              35 90 20 --                             80B  60 70 25  90 60*                                                                              60 85 70  90  100                                                                              15 100                                                                              25 100                            85B  95 100                                                                              65  100                                                                              80 90 100                                                                              100 100 100                                                                              25 100                                                                              85 --                             86B  30 60 20  75 50 50 60 50  65  100                                                                              10 100                                                                              20 80                             87B  0  0  0   100                                                                              45 20 30 60  90  80 0  100                                                                              30 45                             92B  20 80 10  85 15 0  30 100 40  100                                                                              0  60 60 30                             93B  70 100                                                                              25  100                                                                              100                                                                              85 100                                                                              100 100 100                                                                              100                                                                              100                                                                              80 --                             94B  20 70 30  90 80 30 20 100 100 100                                                                              60 30 30 100                            95B  60 90 15  95 95 25 90 100 100 100                                                                              75 100                                                                              70 100                            96B  50 80 0   90 70 30 100                                                                              100 100 100                                                                              40 100                                                                              20 100                            97B  65 100                                                                              35  100                                                                              75 70 80 100 100 100                                                                              50 100                                                                              50 100                            98B  95 100                                                                              65  95 90 100                                                                              95 100 100 90 40 80 60 95                              99B**                                                                             -- 100                                                                              95  90 90*                                                                              90 100                                                                              25  80  40 100                                                                              -- 35 75                             100B 65 75 60  80 75 60 85 100 100 100                                                                              45 100                                                                              65 60                             102B 30 75 20  80 60 0  40 70  100 100                                                                              30 100                                                                              75 --                             __________________________________________________________________________     *Seedling johnsongram (Sorghum halepense) was substituted for roxorange       sorghum.                                                                      **Application rate was 0.56 kg/ha.                                            (--) = Specie did not germinate for some reason.                         

                                      TABLE IV-C                                  __________________________________________________________________________    Pre-Emergence Multi-weed Herbicide Test                                       Application Rate - 1.12 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG SHC                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP                                                                              MD YNS                                                                              CB                               __________________________________________________________________________    2C  0  100                                                                              0   100                                                                              -- 45 70 65  50  100                                                                              15                                                                              100                                                                              90 --                               __________________________________________________________________________     (--) = Not tested.                                                       

                                      TABLE V-C                                   __________________________________________________________________________    Post-Emergence Multi-Weed Herbicidal Activity                                 Application Rate - 1.12 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG SHC                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                              __________________________________________________________________________    2D  0  30 0   100                                                                              -- 0  60 85  95  100                                                                              100                                                                              90 40 --                              __________________________________________________________________________     (--) = Not tested.                                                       

                                      TABLE IV-D                                  __________________________________________________________________________    Pre-Emergence Multi-weed Herbicide Test                                       Application Rate - 2.24 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG SHC                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP                                                                              MD YNS                                                                              CB                               __________________________________________________________________________     7D 100                                                                              100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              100                                                                             100                                                                              95 100                               8D 100                                                                              100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              100                                                                             100                                                                              95 --                               .sup. 16D.sup.a                                                                   70 100                                                                              65  100                                                                              100                                                                              60 98 55  100 100                                                                              90                                                                              100                                                                              90 --                               24D 100                                                                              100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              100                                                                             100                                                                              100                                                                              --                               29D 100                                                                              100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              30                                                                              100                                                                              95 80                               33D 75 15 60  90 90 20 95 100 100 100                                                                              60                                                                              100                                                                              95 100                              53D 100                                                                              100                                                                              100 100                                                                              100                                                                              90 100                                                                              100 100 100                                                                              100                                                                             100                                                                              95 100                              57D 100                                                                              100                                                                              25  100                                                                              100                                                                              30 25 100 100 100                                                                              100                                                                             100                                                                              95 100                              .sup. 64D.sup.a                                                                   -- 0  0   95 35 0  15 50  75  75 25                                                                              -- 75 40                               .sup. 66D.sup.a                                                                   -- 0  15  15 50 20 50 100 100 75 0 -- 90 100                              .sup. 67D.sup.a                                                                   -- 0  0   100                                                                              100                                                                              0  25 95  75  50 25                                                                              -- 30 75                               .sup. 69D.sup.a                                                                   -- 30 0   100                                                                              100                                                                              0  70 100 100 100                                                                              35                                                                              -- 95 100                              .sup. 70D.sup.a                                                                   -- 100                                                                              10  100                                                                              100                                                                              25 65 100 100 100                                                                              0 -- 95 100                              __________________________________________________________________________     (--) = Not tested.                                                            .sup.a Tested at 0.28 kg/ha.                                             

                                      TABLE V-D                                   __________________________________________________________________________    Pre-Emergence Multi-weed Herbicide Test                                       Application Rate - 1.12 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG SHC                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                              __________________________________________________________________________    34D 90 85 30  95 -- 45 98 75  100 100                                                                              40 100                                                                              50 --                              35D 100                                                                              85 70  100                                                                              -- 90 100                                                                              100 100 100                                                                              40 100                                                                              75 --                              40D 100                                                                              100                                                                              20  100                                                                              -- 70 100                                                                              98  98  100                                                                              20 100                                                                              50 --                              41D 100                                                                              100                                                                              80  100                                                                              -- 60 100                                                                              100 100 100                                                                              25 100                                                                              95 --                              42D 50 60 40  85 -- 30 100                                                                              100 100 100                                                                              100                                                                              100                                                                              90 --                              43D 90 95 60  100                                                                              -- 30 98 100 98  100                                                                              45 100                                                                              95 --                              44D 60 100                                                                              20  100                                                                              -- 60 100                                                                              100 90  100                                                                              20 100                                                                              80 --                              45D 95 100                                                                              35  100                                                                              -- 60 90 100 100 100                                                                              0  100                                                                              90 --                              46D 100                                                                              100                                                                              90  100                                                                              -- 95 100                                                                              100 100 100                                                                              40 100                                                                              95 --                              47D 100                                                                              100                                                                              100 100                                                                              -- 98 100                                                                              100 98  100                                                                              30 100                                                                              95 --                              48D 100                                                                              100                                                                              100 100                                                                              -- 100                                                                              100                                                                              100 100 100                                                                              90 100                                                                              100                                                                              --                              49D 100                                                                              100                                                                              100 100                                                                              -- 100                                                                              100                                                                              100 100 100                                                                              90 100                                                                              -- --                              50D 100                                                                              100                                                                              100 100                                                                              100                                                                              85 100                                                                              100 100 100                                                                              90 100                                                                              98 --                              54D 100                                                                              100                                                                              85  100                                                                              100                                                                              15 100                                                                              25  100 100                                                                              65 100                                                                              95 100                             55D 85 100                                                                              35  100                                                                              98 15 100                                                                              15  100 100                                                                              65 100                                                                              95 --                              56D 100                                                                              100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              100                                                                              100                                                                              100                                                                              100                             58D 98 100                                                                              40  95 40 20 95 100 100 100                                                                              85 100                                                                              100                                                                              95                              59D 100                                                                              100                                                                              100 100                                                                              100                                                                              90 100                                                                              100 100 100                                                                              100                                                                              100                                                                              85 80                              60D 100                                                                              100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              75 100                                                                              85 80                              __________________________________________________________________________     (--) = Not tested.                                                       

                                      TABLE VI-D                                  __________________________________________________________________________    Pre-Emergence Multi-weed Herbicide Test                                       Application Rate - 0.56 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG SHC                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                              __________________________________________________________________________    61D -- 100                                                                              65  100                                                                              65 20 80 20  40  80 10 -- 20 0                               62D -- 50 35  70 50 0  0  0   25  50 0  -- 0  0                               63D 100                                                                              100                                                                              100 100                                                                              100                                                                              95 100                                                                              90  95  100                                                                              75 100                                                                              100                                                                              85                              68D -- 0  20  0  0  0  0  60  100 100                                                                              90 -- 75 75                              71D -- 50 40  50 75 40 35 75  50  70 0  -- 75 75                              72D -- 35 60  100                                                                              85 50 100                                                                              25  65  100                                                                              35 -- 100                                                                              35                              73D -- 90 70  100                                                                              95 25 0  70  100 100                                                                              0  -- 50 25                              __________________________________________________________________________     (--) = Not tested.                                                       

                                      TABLE VII-D                                 __________________________________________________________________________    Post-Emergence Multi-Weed Herbicidal Activity                                 Application Rate - 2.24 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG SHC                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                              __________________________________________________________________________     7D 100                                                                              100                                                                              100 100                                                                              80 90 10 95  100 100                                                                              55 100                                                                              45 100                             16D.sup.a                                                                         100                                                                              85 35  100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              100                                                                              100                                                                              85 70                              24D 100                                                                              100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              100                                                                              100                                                                              100                                                                              --                              29D 100                                                                              100                                                                              60  100                                                                              90 100                                                                              100                                                                              100 100 100                                                                              100                                                                              100                                                                              100                                                                              --                              33D 90 98 85  100                                                                              100                                                                              80 100                                                                              100 100 100                                                                              90 100                                                                              90 100                             53D 100                                                                              100                                                                              60  100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              100                                                                              100                                                                              100                                                                              --                              57D 25 40 10  100                                                                              10 0  10 100 95  100                                                                              35 100                                                                              -- 100                             64D.sup.a                                                                         -- 0  0   90 0  0  85 40  100 80 50 -- 35 100                             66D.sup.a                                                                         -- 0  0   65 0  0  70 75  80  75 0  -- 25 75                              67D.sup.a                                                                         -- 0  0   75 35 0  40 70  80  60 0  -- 0  100                             69D.sup.a                                                                         -- 0  0   80 35 0  100                                                                              90  100 100                                                                              40 -- 35 100                             70D.sup.a                                                                         -- 100                                                                              0   100                                                                              70 90 90 100 100 100                                                                              30 -- 25 100                             __________________________________________________________________________     (--) = Not tested.                                                            (.sup.a) Tested at 0.28 kg/ha.                                           

                                      TABLE VIII-D                                __________________________________________________________________________    Post-Emergence Multi-weed Herbicide Test                                      Application Rate - 1.12 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG SHC                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                              __________________________________________________________________________    34D 90 85 30  95 -- 45 98 75  100 100                                                                              40 100                                                                              50 --                              35D 100                                                                              85 70  100                                                                              -- 90 100                                                                              100 100 100                                                                              40 100                                                                              75 --                              40D 75 100                                                                              5   100                                                                              -- 50 75 100 100 100                                                                              40 100                                                                              30 --                              41D-                                                                              -- -- --  -- -- -- -- --  --  -- -- -- -- --                              42D 40 100                                                                              35  100                                                                              -- 50 80 100 100 100                                                                              80 100                                                                              70 --                              43D 60 70 20  100                                                                              -- 55 60 100 100 100                                                                              95 100                                                                              70 --                              44D -- -- --  -- -- -- -- --  --  -- -- -- -- --                              45D -- -- --  -- -- -- -- --  --  -- -- -- -- --                              46D -- -- --  -- -- -- -- --  --  -- -- -- -- --                              47D 90 100                                                                              35  100                                                                              -- 75 90 100 100 100                                                                              25 100                                                                              45 --                              48D 80 100                                                                              60  100                                                                              -- 60 80 100 100 100                                                                              85 100                                                                              60 --                              49D -- -- --  -- -- -- -- --  --  -- -- -- -- --                              50D 90 80 60  95 80 90 100                                                                              100 100 100                                                                              65 100                                                                              80 --                              54D 35 50 30  100                                                                              30 15 90 100 100 100                                                                              100                                                                              100                                                                              95 --                              55D 100                                                                              100                                                                              20  100                                                                              90 20 100                                                                              90  100 100                                                                              100                                                                              100                                                                              -- --                              56D 75 90 75  95 90 25 100                                                                              100 100 100                                                                              90 100                                                                              90 100                             58D 70 100                                                                              40  100                                                                              95 30 95 100 95  100                                                                              95 100                                                                              95 85                              59D 90 100                                                                              95  100                                                                              100                                                                              50 100                                                                              100 100 100                                                                              95 100                                                                              100                                                                              95                              60D 95 100                                                                              100 100                                                                              100                                                                              75 95 100 100 100                                                                              95 100                                                                              100                                                                              100                             __________________________________________________________________________     (--) = Not tested.                                                       

                                      TABLE IX-D                                  __________________________________________________________________________    Post-Emergence Multi-weed Herbicide Test                                      Application Rate - 0.56 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG SHC                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                              __________________________________________________________________________    61D -- 40 0   50 35 0  40 75  95  100                                                                              0  -- 25 50                              62D -- 35 0   20 0  0  20 35  60  100                                                                              0  -- 0  100                             63D 100                                                                              100                                                                              85  98 85 100                                                                              100                                                                              100 100 100                                                                              100                                                                              85 85 95                              68D -- 30 40  85 0  25 60 80  95  100                                                                              95 -- 0  80                              71D -- 50 0   80 65 0  75 100 80  100                                                                              50 -- 25 100                             72D -- 90 70  80 50 50 75 85  100 100                                                                              90 -- 100                                                                              100                             73D -- 100                                                                              15  100                                                                              75 75 85 100 100 90 60 -- 80 100                             __________________________________________________________________________     (--) = Not tested.                                                       

                                      TABLE IV-E                                  __________________________________________________________________________    Pre-Emergence Multi-weed Herbicide Test                                       Application Rate - 2.24 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG JG WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                __________________________________________________________________________    17E 95 85 35  100                                                                              85 25 90 100 100 100                                                                              40 100                                                                              95                                 18E 0  0  0   50 20 0  15 60  45  100                                                                              0  100                                                                              --                                 __________________________________________________________________________

                                      TABLE V-E                                   __________________________________________________________________________    Pre-Emergence Multi-weed Herbicide Test                                       Application Rate - 1.12 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG JG WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                __________________________________________________________________________     7E 30 70 20  100                                                                              75 0  90 100 95  100                                                                              100                                                                              100                                                                              90                                  8E 95 95 45  100                                                                              98 25 90 100 95  100                                                                              90 100                                                                              90                                  9E 10 70 40  100                                                                              20 0  80 100 85  100                                                                              40 100                                                                              95                                 10E 100                                                                              100                                                                              10  100                                                                              40 0  90 100 100 100                                                                              80 100                                                                              100                                11E 90 100                                                                              90  100                                                                              100                                                                              65 100                                                                              100 90  100                                                                              30 100                                                                              65                                 12E 100                                                                              100                                                                              80  100                                                                              100                                                                              85 90 100 100 100                                                                              85 100                                                                              90                                 13E 0  100                                                                              10  100                                                                              100                                                                              80 70 80  90  100                                                                              70 100                                                                              80                                 15E 0  10 0   90 0  0  15 35  30  100                                                                              10 85 75                                 19E 100                                                                              90 0   100                                                                              20 10 40 95  100 100                                                                              100                                                                              100                                                                              65                                 __________________________________________________________________________

                                      TABLE VI-E                                  __________________________________________________________________________    Post-Emergence Multi-Weed Herbicidal Activity                                 Application Rate - 2.24 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG JG WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                __________________________________________________________________________    17E 80 100                                                                              55  95 90 20 60 100 100 100                                                                              75 100                                                                              70                                 18E 0  100                                                                              0   98 20 0  10 70  60  100                                                                              10 100                                                                              45                                 __________________________________________________________________________

                                      TABLE VII-E                                 __________________________________________________________________________    Post-Emergence Multi-Weed Herbicidal Activity                                 Application Rate - 1.12 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG JG WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                __________________________________________________________________________     7E 25 30 0   70 60 20 90 75  95  85 50 100                                                                              35                                  8E 80 80 20  70 70 40 80 50  80  80 60 60 35                                  9E 0  30 0   75 15 25 100                                                                              95  100 100                                                                              60 100                                                                              25                                 10E 60 80 20  70 35 25 80 75  90  90 70 100                                                                              45                                 11E 45 100                                                                              20  100                                                                              100                                                                              40 50 100 100 100                                                                              20 100                                                                              35                                 12E 70 60 30  100                                                                              100                                                                              80 98 90  100 100                                                                              70 98 40                                 13E 25 100                                                                              10  100                                                                              100                                                                              85 100                                                                              80  100 100                                                                              10 90 25                                 15E 30 65 10  90 50 30 20 85  80  98 30 65 15                                 19E 20 60 10  90 10 15 90 100 100 70 100                                                                              40 85                                 __________________________________________________________________________

                                      TABLE IV-F                                  __________________________________________________________________________    Pre-Emergence Multi-weed Herbicide Test                                       Application Rate - 1.12 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG JG WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                              __________________________________________________________________________    19F 40 35 60  100                                                                              90 30 90 100 100 -- 20 100                                                                              90 --                              26F 25 70 45  95 60 25 85 35  75  -- 20 100                                                                              95 90                              27F 45 65 40  100                                                                              60 25 80 100 85  100                                                                              40 100                                                                              95 35                              28F 80 100                                                                              90  100                                                                              100                                                                              90 100                                                                              70  90  100                                                                              30 100                                                                              95 35                              29F 90 45 75  100                                                                              85 40 90 95  90  100                                                                              40 100                                                                              95 --                              30F 90 45 75  100                                                                              90 75 100                                                                              100 80  100                                                                              60 100                                                                              95 --                              31F 60 65 75  100                                                                              100                                                                              55 95 100 100 100                                                                              100                                                                              100                                                                              95 --                              32F 90 100                                                                              90  100                                                                              100                                                                              65 85 100 90  100                                                                              95 100                                                                              85 --                              33F 100                                                                              100                                                                              95  100                                                                              100                                                                              95 100                                                                              100 100 100                                                                              25 100                                                                              90 --                              35F 90 100                                                                              100 100                                                                              -- 90 90 100 90  100                                                                              10 100                                                                              75 --                              36F 90 35 85  100                                                                              -- 15 80 95  90  100                                                                              50 100                                                                              95 --                              39F 100                                                                              100                                                                              100 100                                                                              100                                                                              95 100                                                                              100 100 100                                                                              100                                                                              100                                                                              98 --                              40F 100                                                                              100                                                                              80  100                                                                              100                                                                              70 100                                                                              100 100 100                                                                              90 100                                                                              95 --                              41F 100                                                                              100                                                                              100 100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              60 100                                                                              98 --                              42F 60 100                                                                              85  100                                                                              100                                                                              70 95 100 95  100                                                                              10 100                                                                              95 50                              43F 85 100                                                                              25  100                                                                              60 25 98 100 100 100                                                                              100                                                                              100                                                                              90 100                             44F 0  80 10  85 0  0  75 0   30  100                                                                              0  100                                                                              0  10                              45F 25 100                                                                              40  100                                                                              60 0  65 60  60  100                                                                              50 100                                                                              70 0                               50F -- 100                                                                              50  100                                                                              35 35 75     100 100                                                                              --                                       __________________________________________________________________________     (--) = Not tested.                                                       

                                      TABLE V-F                                   __________________________________________________________________________    Pre-Emergence Multi-weed Herbicide Test                                       Application Rate - 0.56 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG JG WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                              __________________________________________________________________________    46F 0  65 35  75 65 0  0  0   35  100                                                                              25 90 80 0                               47F -- 60 35  100                                                                              100                                                                              0  90 100 100 100                                                                              70 -- 100                                                                              75                              48F -- 75 20  90 60 0  15 70  35  90 0  -- 20 40                              49F -- 60 10  100                                                                              60 0  50 100 95  100                                                                              40 -- 90 100                             51F -- 40 10  95 40 10 50 65  100 100                                                                              0  -- 95 65                              __________________________________________________________________________     (--)  Not tested.                                                        

                                      TABLE VI-F                                  __________________________________________________________________________    Post-Emergence Multi-Weed Herbicidal Activity                                 Application Rate - 2.24 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG JG WO BSG                                                                              AMG SESB                                                                              VL SP MD YNS                                                                              CB                              __________________________________________________________________________    19F 100                                                                              90 65  100                                                                              100                                                                              98 100                                                                              100 100 100                                                                              60 100                                                                              70 100                             26F 60 75 60  95 45 50 90 50  90  100                                                                              40 90 60 --                              27F 80 70 65  95 100                                                                              90 100                                                                              100 100 100                                                                              85 100                                                                              75 --                              28F 80 100                                                                              75  90 85 80 100                                                                              80  80  100                                                                              30 100                                                                              85 85                              29F 85 70 55  90 98 90 100                                                                              100 100 100                                                                              35 100                                                                              60 100                             30F 90 80 40  90 85 80 80 70  100 100                                                                              20 100                                                                              40 --                              31F 100                                                                              80 20  100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              100                                                                              100                                                                              85 --                              32F 70 90 60  100                                                                              100                                                                              98 100                                                                              100 100 100                                                                              100                                                                              100                                                                              60 --                              33F 95 100                                                                              80  100                                                                              90 100                                                                              100                                                                              100 100 100                                                                              70 100                                                                              40 --                              35F 70 90 40  100                                                                              -- 100                                                                              100                                                                              100 100 100                                                                              98 100                                                                              30 --                              36F 85 100                                                                              35  100                                                                              -- 20 100                                                                              100 100 100                                                                              100                                                                              100                                                                              15 --                              39F 100                                                                              100                                                                              85  100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              100                                                                              100                                                                              90 100                             40F 100                                                                              100                                                                              30  100                                                                              100                                                                              100                                                                              100                                                                              100 100 100                                                                              90 100                                                                              75 --                              41F 100                                                                              100                                                                              35  90 70 100                                                                              90 100 100 100                                                                              50 100                                                                              70 --                              42F 45 100                                                                              50  100                                                                              70 55 80 100 100 100                                                                              70 100                                                                              75 100                             43F 25 80 15  98 35 0  20 100 100 100                                                                              100                                                                              100                                                                              60 95                              44F 0  15 0   65 0  0  0  70  100 100                                                                              40 100                                                                              0  100                             45F 0  75 35  70 35 0  60 50  85  100                                                                              50 100                                                                              75 70                              50F -- 40 0   75 45 40 60 100 100 95 30 -- 60 100                             __________________________________________________________________________     (--) = Not tested.                                                       

                                      TABLE VII-F                                 __________________________________________________________________________    Post-Emergence Multi-Weed Herbicidal Activity                                 Application Rate - 0.56 kg/ha                                                 Cmpd.                                                                         No. DB FT ARG WG JG                                                                              WO BSG                                                                              AMG SESB                                                                              VL SP                                                                              MD                                                                              YNS                                                                              CB                                 __________________________________________________________________________    46F 25 35 20  50 35                                                                              35 0  20  75  100                                                                              35                                                                              95                                                                              -- 50                                 47F -- 75 25  90 40                                                                              25 80 100 100 100                                                                              80                                                                              --                                                                              75 100                                48F -- 50 35  80 35                                                                              40 0  75  100 85 15                                                                              --                                                                              50 75                                 49F -- 35 0   75 30                                                                              0  20 100 100 100                                                                              80                                                                              --                                                                              25 85                                 51F -- 35 0   80 35                                                                              20 70 50  95  95 25                                                                              --                                                                              65 50                                 __________________________________________________________________________     (--) = Not Tested.                                                       

The compounds of the present invention and their salts are useful asherbicides and can be applied in a variety of ways at variousconcentrations. In practice, the compounds or salts are formulated intoherbicidal compositions, by admixture, in herbicidally effectiveamounts, with the adjuvants and carriers normally employed forfacilitating the dispersion of active ingredients for agriculturalapplications, recognizing the fact that the formulation and mode ofapplication of a toxicant may affect the activity of the materials in agiven application. Thus, these active herbicidal compounds or salts canbe formulated as granules of relatively large particle size, as wettablepowders, as emulsifiable concentrates, as powdery dusts, as flowables,as solutions or as any of several other known types of formulations,depending upon the desired mode of application. These formulations maycontain as little as about 0.5% to as much as about 95% or more byweight of active ingredient. A herbicidally effective amount dependsupon the nature of the seeds or plants to be controlled and the rate ofapplication varies from about 0.01 to approximately 10 pounds per acre,preferably from about 0.02 to about 4 pounds per acre.

Wettable powders are in the form of finely divided particles whichdisperse readily in water or other dispersants. The wettable powder isultimately applied to the soil either as a dry dust or as a dispersionin water or other liquid. Typical carriers for wettable powders includefuller's earth, kaolin clays, silicas and other readily wet organic orinorganic diluents. Wettable powders normally are prepared to containabout 5% to about 95% of the active ingredient and usually also containa small amount of wetting, dispersing, or emulsifying agent tofacilitate wetting and dispersion.

Emulsifiable concentrates are homogeneous liquid compositions which aredispersible in water or other dispersant, and may consist entirely ofthe active compound or salt with a liquid or solid emulsifying agent, ormay also contain a liquid carrier, such as xylene, heavy aromaticnaphthal, isophorone and other non-volatile organic solvents. Forherbicidal application, these concentrates are dispersed in water orother liquid carrier and normally applied as a spray to the area to betreated. The percentage by weight of the essential active ingredient mayvary according to the manner in which the composition is to be applied,but in general comprises about 0.5% to 95% of active ingredient byweight of the herbicidal composition.

Granular formulations wherein the toxicant is carried on relativelycoarse particles, are usually applied without dilution to the area inwhich suppression of vegetation is desired. Typical carriers forgranular formulations include sand, fuller's earth, attapulgite clay,bentonite clays, montmorillonite clay, vermiculite, perlite and otherorganic or inorganic materials which absorb or which may be coated withthe toxicant. Granular formulations normally are prepared to containabout 0.1% to about 25% of active ingredients which may includesurface-active agents such heavy aromatic naphthas, kerosene or otherpetroleum fractions, or vegetable oils; and/or stickers such asdextrins, glue or synthetic resins.

Typical wetting, dispersing or emulsifying agents and adjuvants used inagricultural formulations include, for example, the alkyl and alkylarylsulfonates and sulfates and their salts; polyhydric alcohols;polyethoxylated alcohols, esters and fatty amines; and other types ofsurface-active agents, many of which are available in commerce. Thesurface-active agent, when used, normally comprises from 0.1% to 30% byweight of the herbicidal composition.

Dusts, which are free-flowing admixtures of the active ingredient withfinely divided solids such as talc, clays, flours and other organic andinorganic solids which act as dispersants and carriers for the toxicant,are useful formulations for soil-incorporating application.

Pastes, which are homogeneous suspensions of a finely divided solidtoxicant in a liquid carrier such as water or oil, are employed forspecific purposes. These formulations normally contain about 5% to about95% of active ingredient by weight, and may also contain small amountsof a wetting, dispersing or emulsifying agent to facilitate dispersion.For application, the pastes are normally diluted and applied as a sprayto the area to be affected.

Other useful formulations for herbicidal applications include simplesolutions of the active ingredient in a dispersant in which it iscompletely soluble at the desired concentration, such as water, acetone,alkylated naphthalenes, xylene and other organic solvents. Pressurizedsprays, typically aerosols, wherein the active ingredient is dispersedin finely-divided form as a result of vaporization of a low boilingdispersant solvent carrier, such as the Freons, may also be used.

The phytotoxic compositions of this invention can be applied to theplants in the conventional manner. Thus, the dust and liquidcompositions can be applied to the plant by the use of power-dusters,boom and hand sprayers and spray dusters. The compositions can also beapplied from airplanes as a dust or a spray or by rope wick applicationsbecause they are effective in very low dosages. In order to modify orcontrol growth of germinating seeds or emerging seedlings, as a typicalexample, the dust and liquid compositions can be applied to the soilaccording to conventional methods and can be distributed in the soil toa depth of at least 1/2 inch below the soil surface. It is not necessarythat the phytotoxic compositions be mechanically admixed with the soilparticles since these compositions can also be applied merely byspraying or sprinkling the surface of the soil. The phytotoxiccompositions of this invention can also be applied by addition toirrigation water supplied to the field to be treated. This method ofapplication permits the penetration of the compositions into the soil asthe water is absorbed therein. Dust compositions, granular compositionsor liquid formulations applied to the surface of the soil can bedistributed below the surface of the soil by conventional means such asdiscing, dragging or mixing operations. In the following examples theherbicidal compound can be substituted with the herbicidal salt of thecompound.

    ______________________________________                                        General Formula                                                               with Ranges     Specific Formula                                              ______________________________________                                        EMULSIFIABLE CONCENTRATE FORMULATIONS                                         Herbicidal                                                                               5-55     herbicidal compound                                                                            24                                       compound            proprietary blend of oil-                                                                      10                                       surfactant(s)                                                                            5-25     soluble sulfonates and                                    solvent(s)                                                                              20-90     polyoxyethylene ethers                                              100%      polar solvent    27                                                           petroleum hydrocarbon                                                                          39                                                                            100%                                     WETTABLE POWDER FORMULATIONS                                                  herbicidal                                                                               3-90     herbicidal compound                                                                            80                                       compound            sodium dialkyl naphthalene                                                                     0.5                                      wetting agent                                                                           0.5-2     sulfonate                                                 dispersing agent                                                                        1-8       sodium lignosulfonate                                                                          7                                        diluent(s)                                                                              8.5-87    attapulgite clay 12.5                                               100%                       100%                                     EXTRUDED GRANULAR FORMULATIONS                                                herbicidal                                                                               1-20     herbicidal compound                                                                            10                                       compound            lignin sulfonate 5                                        binding agent                                                                            0-10     calcium carbonate                                                                              85                                       diluent(s)                                                                              70-99                      100%                                               100%                                                                FLOWABLE FORMULATIONS                                                         herbicidal                                                                              20-70     herbicidal compound                                                                            45                                       compound            polyoxyethylene ether                                                                          5                                        surfactant(s)                                                                            1-10     attagel          0.05                                     suspending                                                                              0.05-1    propylene glycol 10                                       agent(s)            1,2-benzisothiazoline-3-one                                                                    0.03                                     antifreeze agent                                                                         1- 10    silicone defoamer                                                                              0.02                                     antimicrobial                                                                            1-10     water            39.9                                     agent                                100%                                     antifoam agent                                                                          0.1-1                                                               solvent    7.95-77.85                                                                   100%                                                                ______________________________________                                    

When salts are used as the active ingredient in the herbicidalcompositions of this invention it is recommended to use salts that areagriculturally acceptable.

The phytotoxic compositions of this invention can also contain otheradditives, for example, fertilizers, other herbicides and otherpesticides, used as adjuvant or in combination with any of theabove-described adjuvants. Fertilizers useful in combination with theactive ingredients include, for example, ammonium nitrate, urea andsuperphosphate.

We claim:
 1. An intermediate compound of the structural formula##STR96## wherein R⁶⁰ is hydrogen; halogen; C₁ -C₂ alkyl; C₁ -C₂ alkoxy;nitro; cyano; C₁ -C₂ haloalkyl; or R^(a) SO_(n) -- wherein n is 0 or 2and R^(a) is C₁ -C₂ alkyl, trifluoromethyl or difluoromethyl; ortrifluoromethoxy or difluoromethoxy;R⁶¹ is hydrogen or C₁ -C₄ alkyl; R⁶²is hydrogen or C₁ -C₄ alkyl; or R⁶¹ and R⁶² together are C₂ -C₅alkylene; R⁶³ is C₁ -C₄ alkyl; R⁶⁴ is C₁ -C₄ alkyl; or R⁶³ and R⁶⁴together are C₂ -C₅ alkylene; R⁶⁵ and R⁶⁶ independently are (1)hydrogen; (2) halogen; (3) C₁ -C₄ alkyl; (4) C₁ -C₄ alkoxy; (5)trifluoromethoxy; (6) cyano; (7) nitro; (8) C₁ -C₄ haloalkyl; (9) R^(b)SO_(n) -- wherein n is the integer 0, 1 or 2; and R^(b) is (a) C₁ -C₄alkyl; (b) C₁ -C₄ alkyl substituted with halogen or cyano; (c) phenyl;or (d) benzyl; (10) --NR^(c) R^(d) wherein R^(c) and R^(d) independentlyare hydrogen or C₁ -C₄ alkyl; (11) R^(e) C(O)-- wherein R^(e) is C₁ -C₄alkyl or C₁ -C₄ alkoxy; or (12) --SO₂ NR^(c) R^(d) wherein R^(c) andR^(d) are as defined; and (13) --N(R^(c))C(O)R^(d) wherein R^(c) andR^(d) are as defined.